Regional divergent synthesis method of alpha-amino acid and / or beta-amino acid derivative

Abstract

The invention belongs to the technical field of organic chemistry, and discloses a method for regiodivergent synthesis of alpha-amino acid and / or beta-amino acid derivatives. The method comprises the following steps: in an air atmosphere, taking an organic solvent as a reaction medium, and reacting a carboxylic acid compound, organic boric acid and a dioxazolone compound under the action of a catalyst, silver salt and an alkaline compound to obtain the alpha-amino acid and / or beta-amino acid derivative. The method is simple, efficient, low in price, wide in substrate applicability, high in yield and mild in reaction condition, and alpha-amino acid and / or beta-amino acid derivatives are / is synthesized in a regional divergence mode.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing α-amino acid and / or β-amino acid derivatives in a regio-divergent manner. Background Art

[0002] Amino acids have the characteristics of high sensitivity, strong specificity, diverse functions and flexible use. They play a vital role in drug development, biomedical research, protein modification and other aspects. α-Amino acids are almost indispensable and play an increasingly important role in the fields of pharmaceuticals, biology and materials science. JNJ-A07 is a pan-serotype dengue virus (DENV) inhibitor that has been shown to have activity in treating dengue virus infection in mouse models. This molecule is not prone to drug-resistant mutations and targets the interaction between viral NS3 and NS4B, thereby preventing the formation of the viral replication complex. Eluxadoline is a gastrointestinal drug used to treat diarrhea-predominant irritable bowel syndrome (IBS-D). They are all unnatural α-amino acids. Therefore, establishing an effective method for the artificial synthesis of unnatural α-amino acid derivatives is one of the essential and urgent research topics.

[0003] Although β-amino acids are less abundant than α-amino acids, they are common motifs in many natural products and have valuable pharmacological properties, such as antibacterial (Prabhakaran, PC; Woo, N.-T.; Yorgey, PS; Gould, SJ. Biosynthesis of Blasticidin S from L-α-arginine. Stereochemistry in the arginine-2,3-aminomutase reaction. J. Am. Chem. Soc. 1988, 110, 5785-5791.), anti-tuberculosis (Yin, X.; O'Hare, T.; Gould, SJ; Zabriskie, T. Identification and cloning of genes encoding viomycin biosynthesis from Streptomyces vinaceus and evidence for involvement of a rare oxygenase. Gene 2003, 312, 215-224.), antibiotics (Liu, W.; Christenson, SD; Standage, S.; Shen, B. Biosynthesis of the enediyne antitumor antibiotic C-1027. Science 2002, 297, 1170-1173.) and antitumor activities (Wani, MC; Taylor, HL; Wall, ME; Coggon, P.; McPhail, ATPlant antitumoragents. VI. Isolation and structure of taxol, a novel antileukemic and antitumoragent from Taxus brevifolia. J. Am. Chem. Soc. 1971, 93, 2325-2327.). β-Amino acids are precursors of various biologically active compounds and key components in drug molecules. For example: Sitagliptin is a new anti-type II diabetes drug approved by the FDA and is the first dipeptidyl peptidase-IV inhibitor drug used to treat type II diabetes.It is effective orally and has good market prospects. It has a significant blood sugar-lowering effect when used alone or in combination with metformin or pioglitazone. It is safe to take, well tolerated, and has few adverse reactions. Influenza virus inhibitor is an effective and selective influenza virus inhibitor that shows antiviral and NA (neuraminidase) inhibitory activity. Protein kinase inhibitor is a class of compounds that can inhibit the activity of protein tyrosine kinase.

[0004] Sitagliptin: Influenza virus inhibitor: Protein kinase inhibitor:

[0005] Because α- and β-amino acid derivatives are found in numerous bioactive compounds, pharmaceuticals, and natural products with remarkable biologically relevant properties, there is growing interest in synthesizing unnatural α- and β-amino acid derivatives. However, the regio-divergent construction of α- and β-amino acid derivatives using readily available and inexpensive starting materials under mild conditions remains a long-standing challenge in synthetic chemistry. Summary of the Invention

[0006] In response to the problems and shortcomings of the prior art, the present invention aims to provide a simple, efficient, and regio-divergent method for preparing α-amino acid and / or β-amino acid derivatives. The present invention utilizes inexpensive and readily available carboxylic acid compounds, dioxazolones, and a variety of organic boronic acids as raw materials. In the presence of a rhodium or ruthenium catalyst, a silver salt, and a base, the reaction proceeds at room temperature to obtain α-amino acid and / or β-amino acid derivatives. The method of the present invention has the advantages of low cost, wide substrate applicability, high atom economy, and the synthesized products have potential pharmaceutical value. The method of the present invention is simple, efficient, and regio-divergent, successfully synthesizing α-amino acid and β-amino acid derivatives.

[0007] The purpose of the present invention is achieved through the following technical solutions:

[0008] A method for regiodivergent synthesis of α-amino acid and / or β-amino acid derivatives, comprising the following steps:

[0009] In an air atmosphere, with an organic solvent as the reaction medium, a carboxylic acid compound, a dioxazolone compound and an organic boronic acid react in the presence of a catalyst, a silver salt and an alkaline compound to obtain α-amino acid and / or β-amino acid derivatives.

[0010] The carboxylic acid compound is

[0011] In the carboxylic acid compound, the R1 is hydrogen, benzyl, alkyl, or substituted alkyl;

[0012] The alkyl group includes methyl, ethyl, propyl, and isopropyl; the substituted alkyl group is chloropentyl.

[0013] The R 2 is methyl, ethyl or propyl.

[0014] The organic boronic acid is 4-Dibenzofuranboronic acid

[0015] R 3 It is hydrogen, methyl, methoxy, fluorine, chlorine, bromine, trifluoromethoxy, or furyl.

[0016] R 4 It is hydrogen, methyl, acetyl, trifluoromethyl, methoxy, nitro, fluorine, chlorine or bromine.

[0017] R 5 is hydrogen, methoxy, trifluoromethoxy, phenyl, trifluoromethyl, vinyl, fluorine, chlorine, bromine, iodine, ester group, acetoxy group, amide group, cyano group; the ester group is -COOCH3; the amide group is -CON(R')(R"), R' and R" are methyl groups.

[0018] R 6 is hydrogen, methyl, methoxy, fluorine, or bromine;

[0019] X is F, Cl, Br, or I.

[0020] The dioxazolone compound is

[0021]

[0022] The R 7 is a substituted or unsubstituted aryl or alkyl group.

[0023] The substituted or unsubstituted aryl group is phenyl, 4-chlorophenyl, 3-fluorophenyl, 4-methoxyphenyl, or 2-thienyl.

[0024] The alkyl group is C 1-6 alkyl.

[0025] The molar ratio of the organic boronic acid, the carboxylic acid compound and the dioxazolone compound is (1-2): (1-2): (1-2).

[0026] The rhodium or ruthenium catalyst is one or more of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer and p-cymene dichlororuthenium(II) dimer.

[0027] The molar ratio of the catalyst to the organic boronic acid compound is (0.005-0.02):1.

[0028] The silver salt is one or more of silver carbonate, silver nitrate, silver benzoate, silver hexafluoroantimonate, silver trifluoroacetate, silver trifluoromethanesulfonate, silver acetate, and silver tetrafluoroborate, preferably one or more of silver carbonate and silver acetate.

[0029] The molar ratio of the silver salt to the organic boronic acid compound is (0.05-0.6):1.

[0030] The alkaline compound is one or more of sodium acetate, copper acetate, cesium acetate, lithium acetate, potassium acetate, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium methoxide, and sodium benzoate, preferably one or more of sodium carbonate and cesium acetate.

[0031] The organic solvent is one or more of tetrahydrofuran (THF), 1,4-dioxane, hexafluoroisopropanol (HFIP), trifluoroethanol (TFE), toluene, dichloromethane, dichloroethane, acetone, N,N-dimethylformamide (DMF), preferably one or more of tetrahydrofuran (THF) and hexafluoroisopropanol (HFIP).

[0032] The organic solvent is one or more of tetrahydrofuran (THF), 1,4-dioxane, dichloromethane, dichloroethane, and acetone, and the reaction obtains an α-amino acid derivative; the organic solvent is one or more of hexafluoroisopropanol (HFIP) and trifluoroethanol (TFE), and the reaction obtains a β-amino acid derivative.

[0033] Furthermore, when the silver salt is silver carbonate and the alkaline compound is sodium carbonate, a high yield of α-amino acid derivatives can be obtained; when the silver salt is silver carbonate or silver acetate and the alkaline compound is cesium acetate, a high yield of β-amino acid derivatives can be obtained.

[0034] The reaction temperature is room temperature (23-30° C.), and the reaction time is 20-28 h.

[0035] After the reaction is completed, subsequent treatment is performed, which includes quenching the reaction, extracting with ethyl acetate, removing the solvent in the organic phase, and separating by column chromatography. The removal of the solvent in the organic phase includes removing water from the organic phase and then removing the organic solvent.

[0036] The quenching reaction refers to adding a saturated sodium chloride solution to the reaction system; the removing of water from the organic phase refers to drying with a desiccant, which is anhydrous sodium sulfate, and then filtering; the removing of the organic solvent from the organic phase refers to removing the organic solvent by distillation under reduced pressure.

[0037] The eluent of the column chromatography is a mixed solvent of petroleum ether, ethyl acetate and formic acid, and the volume ratio of petroleum ether to ethyl acetate is (50-100):(15-40):1.

[0038] Carboxylic acid compounds The general structural formula of the organic boronic acid is: 8 B(OH)2,R 8 Corresponding to the groups in the organic boronic acid structure provided above; the dioxazolone compound is

[0039]

[0040] The carboxylic acid compound is The structure of the α-amino acid derivative is

[0041] The carboxylic acid compound is The structure of the β-amino acid derivative is The carboxylic acid compound is The structure of β-amino acid derivatives is

[0042] The chemical reaction equation of the synthesis method of the present invention is: For example,

[0043]

[0044] The synthesis method of the present invention has the following advantages and beneficial effects:

[0045] (1) The method of the present invention uses metal rhodium or ruthenium as a catalyst, and has the advantages of high yield, wide substrate applicability, and rich product value; the method of the present invention uses cheap and easily available carboxylic acid as a raw material, is simple to operate, and has high economic value; and uses organic boronic acid and dioxazolone as raw materials, and has the advantages of cheap raw materials, easy preparation, commercial availability, and high atom economy.

[0046] (2) The synthetic method of the present invention allows for the divergent synthesis of α-amino acid and β-amino acid derivatives through a single reaction. The inherent modularity and versatility of the present method provide ample opportunities for easily constructing diverse libraries of α-amino acid and β-amino acid derivatives. The method of the present invention has broad substrate adaptability, mild conditions, can react in air, and requires minimal catalyst, thus promising practical application in large-scale production. BRIEF DESCRIPTION OF THE DRAWINGS

[0047] Figure 1 is the hydrogen spectrum of the target product obtained in Example 1;

[0048] Figure 2 is the hydrogen spectrum of the target product obtained in Example 3;

[0049] Figure 3 is the hydrogen spectrum of the target product obtained in Example 5;

[0050] Figure 4 is the hydrogen spectrum of the target product obtained in Example 6;

[0051] Figure 5 is the hydrogen spectrum of the target product obtained in Example 7;

[0052] Figure 6 is the hydrogen spectrum of the target product obtained in Example 8;

[0053] Figure 7 is the hydrogen spectrum of the target product obtained in Example 9;

[0054] Figure 8 is the hydrogen spectrum of the target product obtained in Example 12;

[0055] Figure 9 This is the hydrogen spectrum of the target product obtained in Example 14. DETAILED DESCRIPTION

[0056] The present invention will be described in further detail below with reference to the embodiments and drawings, but the embodiments of the present invention are not limited thereto.

[0057] In the examples, when tetrahydrofuran (THF) is used as the solvent, the silver salt is silver carbonate, and the base is sodium carbonate, a high yield of α-amino acid derivatives can be obtained. When hexafluoroisopropanol (HFIP) is used as the solvent, the silver salt is silver carbonate or silver acetate, and the base is cesium acetate, a high yield of β-amino acid derivatives can be obtained.

[0058] In the example of obtaining α-amino acid derivatives, the reaction molar ratio of carboxylic acid compound, organic boronic acid and dioxazolone compound is 1.5:1:1.2; in the example of obtaining β-amino acid derivatives, the reaction molar ratio of carboxylic acid compound, arylboronic acid and dioxazolone compound is 1.5:1:1.5.

[0059] Example 1

[0060] Under air atmosphere, 0.24 mmol of phenyldioxazolone, 0.2 mmol of phenylboronic acid, 0.3 mmol of trans-3-hexenoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of sodium carbonate, and 1.0 ml of tetrahydrofuran were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the desired product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 80:20:1, with a yield of 87%.

[0061] The structural characterization data of the obtained product are as follows:

[0062] 1 H NMR (500 MHz, Chloroform-d) δ 7.52-7.42 (m, 3H), 7.37-7.31 (m, 2H), 7.26 (d, J = 6.4 Hz, 2H), 7.22-7.14 (m, 3H), 6.49 (s, 1H), 4.62 (s, 1H), 2.69-2.58 (m, 1H), 2.42-2.31 (m, 1H), 2.17-2.06 (m, 1H), 1.80-1.71 (m, 1H), 1.63-1.52 (m, 1H), 0.73 (t, J = 7.1 Hz, 3H). Figure 1 shown.

[0063] 13 C NMR (126MHz, Chloroform-d) δ175.8,167.6,144.5,133.3,131.8,128.7,128.4,127.8,127.1,126.5,53.0,45.1,38.3,30.1,11.8.

[0064] The structure of the product is inferred based on the above data:

[0065]

[0066] Example 2

[0067] Under air atmosphere, 0.24 mmol of phenyldioxazolone, 0.2 mmol of phenylboronic acid, 0.3 mmol of vinylacetic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of sodium carbonate, and 1.0 ml of tetrahydrofuran were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the desired product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 80:20:1, with a yield of 74%.

[0068] The structural characterization data of the obtained product are as follows:

[0069] 1 H NMR (500MHz, DMSO-d6) δ12.25(s,1H),8.37(d,J=8.2Hz,1H),7.76(d,J=7.6Hz,2H),7.51(t,J=7.3Hz,1H),7.44(t,J=7.5Hz ,2H),7.31-7.21(m,4H),7.18(t,J=7.2Hz,1H),4.55-4.44(m,1H),2.95-2.80(m,2H),2.60-2.52(m,1H),2.49-2.42(m,1H).

[0070] 13 C NMR (126MHz, DMSO-d6) δ173.0,166.1,139.2,135.1,131.5,129.6,128.7,128.6,127.6,126.6,48.7,40.4,39.3.

[0071] The structure of the product is inferred based on the above data:

[0072]

[0073] Example 3

[0074] Under air atmosphere, 0.24 mmol of phenyldioxazolone, 0.2 mmol of 4-cyanophenylboronic acid, 0.3 mmol of trans-3-hexenoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of sodium carbonate, and 1.0 ml of tetrahydrofuran were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the desired product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 80:20:1, with a yield of 74%.

[0075] The structural characterization data of the obtained product are as follows:

[0076] 1 H NMR (500 MHz, Chloroform-d) δ7.60 (d, J = 7.4 Hz, 2H), 7.50 (d, J = 7.1 Hz, 3H), 7.39 (t, J = 7.5 Hz, 2H), 7.28 (d, J = 8.8 Hz, 2H), 6.74 (d, J = 6.9 Hz, 1H), 4.64 (s, 1H), 2.73 (s, 1H), 2.35 (d, J = 13.6 Hz, 1H), 2.19-2.06 (m, 1H), 1.81-1.70 (m, 1H), 1.62-1.49 (m, 1H), 0.71 (t, J = 7.1 Hz, 3H). Figure 2 shown.

[0077] 13 C NMR (126MHz, Chloroform-d) δ175.6,167.7,150.0,133.0,132.3,132.3,128.7,128.6,127.0,119.0,110.1,51.9,44.9,38.2,29.7,11.7.

[0078] The structure of the product is inferred based on the above data:

[0079]

[0080] Example 4

[0081] Under air atmosphere, 0.24 mmol of phenyldioxazolone, 0.2 mmol of 2-fluoro-5-pyridineboronic acid, 0.3 mmol of trans-3-hexenoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of sodium carbonate, and 1.0 ml of tetrahydrofuran were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 80:20:1, with a yield of 70%.

[0082] The structural characterization data of the obtained product are as follows:

[0083] 1 H NMR (500MHz, DMSO-d6) δ8.44(s,1H),8.07(s,1H),7.87(td,J=8.3,2.5Hz,1H),7.80(d,J=7.6Hz,2H), 7.75(d,J=7.6Hz,1H),7.52(q,J=5.8,4.4Hz,1H),7.45(t,J=7.6Hz,2H),7.07(dd,J=8.5,2.7Hz,1H),4 .32(q,J=7.8Hz,1H),2.74(dq,J=12.6,7.2Hz,1H),2.21(dt,J=13.5,6.6Hz,1H),1.99(dt,J=14.2,8.3 Hz,1H),1.74(ddd,J=13.1,7.6,5.3Hz,1H),1.54(ddd,J=13.6,9.3,6.9Hz,1H),0.67(t,J=7.3Hz,3H).

[0084] 13 C NMR (126MHz, DMSO-d6) δ175.7, 166.5, 162.2 (d, J = 233.6Hz), 147.3 (d, J = 14.5Hz), 141.3 (d, J = 7.8 Hz), 138.7, 131.7, 128.8, 128.6, 127.8, 127.3, 109.5 (d, J = 37.5Hz), 51.8, 40.9, 40.4, 28.1, 12.0.

[0085] Based on the above data, the structure of the obtained product is inferred:

[0086]

[0087] Example 5

[0088] Under air atmosphere, 0.24 mmol of phenyldioxazolone, 0.2 mmol of 3-fluoro-5-methoxyphenylboronic acid, 0.3 mmol of trans-3-hexenoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of sodium carbonate, and 1.0 ml of tetrahydrofuran were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 80:20:1, with a yield of 70%.

[0089] The structural characterization data of the obtained product are as follows:

[0090] 1 H NMR (500 MHz, DMSO-d6) δ 12.62 (s, 1H), 8.58 (d, J = 7.8 Hz, 1H), 7.82 (d, J = 7.6 Hz, 2H), 7.54 (t, J = 7.3 Hz, 1H), 7.46 (t, J = 7.6 Hz, 2H), 6.69-6.56 (m, 3H), 4.38-4.30 (m, 1H), 3.73 (s, 3H), 2.67-2.58 (m, 1H), 2.22-2.11 (m, 1H), 2.04-1.95 (m, 1H), 1.74-1.65 (m, 1H), 1.59-1.49 (m, 1H), 0.69 (t, J = 7.3 Hz, 3H). Figure 3 shown.

[0091] 13 C NMR (126MHz, DMSO-d6) δ174.3, 166.8, 163.5 (d, J = 241.9Hz), 160.9 (d, J = 11.7Hz), 148.7 (d, J = 9.1Hz), 133.1 (d, J = 322.1H z), 128.3 (d, J = 94.5Hz), 110.5 (d, J = 2.4Hz), 106.7 (d, J = 21.2Hz), 99.4 (d, J = 25.2Hz), 55.9, 51.4, 44.3, 37.6, 27.8, 12.2.

[0092] The structure of the product is inferred based on the above data:

[0093]

[0094] Example 6

[0095] Under air atmosphere, 0.3 mmol of phenyldioxazolone, 0.2 mmol of phenylboronic acid, 0.3 mmol of trans-3-hexenoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of cesium acetate, and 1.0 ml of hexafluoroisopropanol were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 50:20:1, with a yield of 81%.

[0096] The structural characterization data of the obtained product are as follows:

[0097] 1 H NMR (500 MHz, Chloroform-d) δ7.53 (d, J = 7.5 Hz, 2H), 7.45 (t, J = 7.5 Hz, 1H), 7.34 (q, J = 7.5 Hz, 4H), 7.23 (t, J = 9.0 Hz, 3H), 6.34 (d, J = 9.0 Hz, 1H), 4.77 (m, 1H), 2.91 (m, 1H), 2.70 (m, 1H), 2.61 (m, 1H), 1.88 (m, 1H), 1.74 (m, 1H), 0.83 (t, J = 7.5 Hz, 3H). Figure 4 shown.

[0098] 13 C NMR (126MHz, Chloroform-d) δ175.2,167.3,140.1,134.2,131.6,128.7,128.63,128.59,127.2,126.8,50.9,49.9,37.9,25.2,12.1.

[0099] The structure of the product is inferred based on the above data:

[0100]

[0101] Example 7

[0102] Under air atmosphere, 0.3 mmol of phenyldioxazolone, 0.2 mmol of phenylboronic acid, 0.3 mmol of vinylacetic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of cesium acetate, and 1.0 ml of hexafluoroisopropanol were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the desired product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 50:20:1, with a yield of 97%.

[0103] The structural characterization data of the obtained product are as follows:

[0104] 1 H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.35 (d, J = 8.5 Hz, 1H), 7.76 (d, J = 7.5 Hz, 2H), 7.47 (m, 3H), 7.26 (m, 4H), 7.21-7.16 (m, 1H), 4.51 (m, 1H), 2.88 (m, 2H), 2.61-2.43 (m, 2H). Figure 5 shown.

[0105] 13 C NMR (126MHz, DMSO-d6) δ172.9,166.2,139.2,135.2,131.5,129.6,128.7,128.6,127.6,126.6,48.7,39.5,39.3.

[0106] The structure of the product is inferred based on the above data:

[0107]

[0108] Example 8

[0109] Under air atmosphere, 0.3 mmol of phenyldioxazolone, 0.2 mmol of phenylboronic acid, 0.3 mmol of (E)-5-phenylpent-3-enoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of cesium acetate, and 1.0 ml of hexafluoroisopropanol were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 50:20:1, with a yield of 70%.

[0110] The structural characterization data of the obtained product are as follows:

[0111] 1 H NMR (500 MHz, DMSO-d6) δ 12.16 (s, 1H), 8.25 (d, J = 8.5 Hz, 1H), 7.78-7.71 (m, 2H), 7.49 (t, J = 7.5 Hz, 1H), 7.43 (t, J = 7.5 Hz, 2H), 7.24 (m, 4H), 7.11 (m, 3H), 7.08-6.97 (m, 3H), 4.65 (m, 1H), 3.40-3.28 (m, 1H), 3.17 (m, 1H), 2.99 (m, 1H), 2.63-2.55 (m, 2H). Figure 6 shown.

[0112] 13 C NMR(126MHz,DMSO-d6)δ173.2,166.5,141.2,141.0,135.4,131.4,129.3,1 29.2,128.6,128.42,128.40,127.7,126.7,126.0,51.9,51.4,36.4,36.0.

[0113] The structure of the product is inferred based on the above data:

[0114]

[0115] Example 9

[0116] Under air atmosphere, 0.3 mmol of phenyldioxazolone, 0.2 mmol of phenylboronic acid, 0.3 mmol of 3-cyclopentenecarboxylic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of cesium acetate, and 1.0 ml of hexafluoroisopropanol were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 50:20:1, with a yield of 72%.

[0117] The structural characterization data of the obtained product are as follows:

[0118] 1 H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.45 (d, J = 8.4 Hz, 1H), 7.88-7.74 (m, 2H), 7.56-7.42 (m, 3H), 7.40-7.28 (m, 4H), 7.21 (t, J = 7.2 Hz, 1H), 4.85-4.74 (m, 1H), 3.21-3.11 (m, 1H), 3.11-3.00 (m, 1H), 2.34-2.26 (m, 1H), 2.26-2.18 (m, 1H), 2.18-2.09 (m, 1H), 2.08-1.98 (m, 1H). Figure 7 shown.

[0119] 13 C NMR (126MHz, DMSO-d6) δ175.0,166.5,144.6,135.3,131.5,128.8,128.5,127.9,127.6,126.6,51.5,47.8,42.9,39.7,36.7.

[0120] The structure of the product is inferred based on the above data:

[0121]

[0122] Example 10

[0123] Under air atmosphere, 0.3 mmol of phenyldioxazolone, 0.2 mmol of 4-dibenzofuranboronic acid, 0.3 mmol of vinylacetic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of cesium acetate, and 1.0 ml of hexafluoroisopropanol were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 50:20:1, with a yield of 70%.

[0124] The structural characterization data of the obtained product are as follows:

[0125] 1 H NMR (500MHz, DMSO-d6) δ12.23(s,1H),8.40(d,J=8.5Hz,1H),8.11(d,J=7.5Hz,1H),7.97(d,J=7.5Hz,1H),7.72(d,J=7.5Hz ,2H),7.61(m,1H),7.49(m,2H),7.38(m,4H),7.30(m,1H),4.79(m,1H),3.41-3.29(m,1H),3.29-3.17(m,1H),2.62(m,2H).

[0126] 13 C NMR (126MHz, DMSO-d6) δ172.9,166.2,155.8,155.0,135.1,131.4,129.1,128.6,127. 8,127.6,124.4,123.7,123.42,123.38,123.0,121.6,119.7,112.0,47.4,39.4,34.5.

[0127] The structure of the product is inferred based on the above data:

[0128]

[0129] Example 11

[0130] Under air atmosphere, 0.3 mmol of phenyldioxazolone, 0.2 mmol of 4-acetoxyphenylboronic acid, 0.3 mmol of trans-3-hexenoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of cesium acetate, and 1.0 ml of hexafluoroisopropanol were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the desired product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 50:20:1, with a yield of 80%.

[0131] The structural characterization data of the obtained product are as follows:

[0132] 1 H NMR(500MHz,Chloroform-d)δ9.81(s,1H),7.55-7.50(m,2H),7.44-7.39(m,1H),7.32(t,J= 7.6Hz,2H),7.21(d,J=8.3Hz,2H),7.03(d,J=8.3Hz,2H),6.63(d,J=9.3Hz,1H),4.74(dq,J=1 1.3, 6.1Hz, 1H), 2.93 (dt, J=10.8, 5.4Hz, 1H), 2.64 (qd, J=16.1, 5.7Hz, 2H), 2.25 (s, 3H), 1. 85(ddt,J=13.8,7.4,3.6Hz,1H), 1.67(ddd,J=13.8,10.0,7.2Hz,1H), 0.79(t,J=7.3Hz,3H).

[0133] 13 C NMR (126MHz, Chloroform-d) δ175.5,169.6,167.6,149.6,137.9,134.2,131.6,129.5,128.6,126.9,121.6,50.3,50.0,37.2,25.2,21.1,12.0.

[0134] The structure of the product obtained is inferred from the above data as follows:

[0135]

[0136] Example 12

[0137] Under air atmosphere, 0.3 mmol of phenyldioxazolone, 0.2 mmol of 4-methoxycarbonylphenylboronic acid, 0.3 mmol of trans-3-hexenoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of cesium acetate, and 1.0 ml of hexafluoroisopropanol were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 50:20:1, with a yield of 79%.

[0138] The structural characterization data of the obtained product are as follows:

[0139] 1 H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.17 (d, J = 8.6 Hz, 1H), 7.89 (d, J = 7.9 Hz, 2H), 7.66 (d, J = 7.6 Hz, 2H), 7.47 (t, J = 7.3 Hz, 1H), 7.40 (t, J = 7.5 Hz, 4H), 4.68-4.51 (m, 1H), 3.82 (s, 3H), 2.98-2.88 (m, 1H), 2.58-2.52 (m, 1H), 2.50-2.44 (m, 1H), 1.93-1.79 (m, 1H), 1.75-1.63 (m, 1H), 0.70 (t, J = 7.3 Hz, 3H). Figure 8 shown.

[0140] 13 C NMR (126MHz, DMSO-d6) δ173.1,166.7,166.2,148.0,135.2,131.4,129.5,129.4,128.6,128.1,127.6,52.4,51.7,51.0,37.2,23.6,12.6.

[0141] Based on the above data, the structure of the obtained product is inferred:

[0142]

[0143] Example 13

[0144] Under air atmosphere, 0.3 mmol of 4-chlorophenyldioxazolone, 0.2 mmol of phenylboronic acid, 0.3 mmol of trans-3-hexenoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of cesium acetate, and 1.0 ml of hexafluoroisopropanol were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 50:20:1, with a yield of 90%.

[0145] The structural characterization data of the obtained product are as follows:

[0146] 1 H NMR (500MHz, DMSO-d6) δ12.10(s,1H),8.23(d,J=8.4Hz,1H),7.70(d,J=8.1Hz,2H),7.49(d,J=8.1Hz,2H),7.29(t,J=7.5Hz,2H),7.23(d,J=7.6Hz,2 H),7.18(t,J=7.3Hz,1H),4.66-4.44(m,1H),2.87-2.78(m,1H),2.45(d,J =7.8Hz,2H),1.86-1.75(m,1H),1.69-1.57(m,1H),0.70(t,J=7.2Hz,3H).

[0147] 13 C NMR (126MHz, DMSO-d6) δ165.1,141.9,136.1,134.1,129.6,129.0,128.6,128.5,126.7,51.6,51.5,37.0,23.3,12.8.

[0148] The structure of the product is inferred based on the above data:

[0149]

[0150] Example 14

[0151] Under air atmosphere, 0.3 mmol of methyldioxazolone, 0.2 mmol of 2,4,5-trifluorophenylboronic acid, 0.3 mmol of vinylacetic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of cesium acetate, and 1.0 ml of hexafluoroisopropanol were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 50:20:1, with a yield of 71%.

[0152] The structural characterization data of the obtained product are as follows:

[0153] 1 H NMR (500 MHz, DMSO-d6) δ 12.37 (s, 1H), 7.84 (d, J = 8.6 Hz, 1H), 7.52-7.43 (m, 1H), 7.37-7.27 (m, 1H), 4.27 (q, J = 6.9 Hz, 1H), 2.87-2.77 (m, 1H), 2.70-2.60 (m, 1H), 2.44-2.31 (m, 2H), 1.70 (s, 3H). Figure 9 shown.

[0154] 13 C NMR(126MHz, DMSO-d6)δ172.7,169.0,157.8-157.2(m),155.6-155.2(m),149.3(d,J=14.6Hz),147.3(d, J=14.4Hz),123.3-120.8(m),119.7(dd,J=18.9,6.1Hz),106.2,106.02,105.95,105.8,46.4,32.9,23.1.

[0155] The structure of the product is inferred based on the above data:

[0156]

[0157] Application of Amino Acids: Preparation of N-Ac Sitagliptin: Under a nitrogen atmosphere, a stirrer, 0.22 mmol of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, and 0.2 mmol of the product from Example 14 were added to a reaction vessel. 0.6 ml of N,N-dimethylformamide was then added, followed by 0.6 mmol of triethylamine, 0.3 mmol of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, and 0.3 mmol of 1-hydroxybenzotriazole. The vial was sealed and allowed to stand at room temperature overnight. After the reaction, the reaction mixture was quenched with a semi-saturated aqueous sodium bicarbonate solution, extracted with dichloromethane, and the organic phases were combined, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated. Purification was achieved by column chromatography. The column chromatography eluent was a 1:9 volume ratio methanol:dichloromethane mixed solvent, yielding 75%.

[0158] The structural characterization data of the obtained N-Ac Sitagliptin are as follows:

[0159] 1 H NMR(500MHz,DMSO-d6)δ7.81(t,J=9.9Hz,1H),7.51-7.30(m,2H),4.99(d,J=2.8Hz,1H),4.93-4.80(m,1H),4.36-4 .20(m,2H),4.08(q,J=5.6Hz,1H),4.01-3.89(m,2H),2.92-2.82(m,1H),2.73-2.57(m,3H),1.65(d,J=41.9Hz,3H);

[0160] 19 F NMR(471MHz, DMSO-d6)δ-61.9(d,J=19.4Hz),-118.6(t,J=15.0Hz),-137.3--137.5(m),-144.2(ddd,J=32.1,22.7,15.5Hz).

[0161] The structure of the product is inferred based on the above data:

[0162]

[0163] Example 15

[0164] Under air atmosphere, 0.24 mmol of phenyldioxazolone, 0.2 mmol of phenylboronic acid, 0.3 mmol of trans-3-hexenoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver carbonate, 0.1 mmol of sodium carbonate, and 1.0 ml of chloroform were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 80:20:1, with a yield of 22%.

[0165] The structural characterization data of the obtained product are as follows:

[0166] 1 H NMR(500MHz,Chloroform-d)δ7.52-7.42(m,3H),7.37-7.31(m,2H),7.26(d,J=6.4Hz,2H),7.22-7.14(m,3H),6.49(s,1H),4.6 2(s,1H),2.69-2.58(m,1H),2.42-2.31(m,1H),2.17-2.06(m,1H),1.80-1.71(m,1H),1.63-1.52(m,1H),0.73(t,J=7.1Hz,3H).

[0167] 13 C NMR (126MHz, Chloroform-d) δ175.8,167.6,144.5,133.3,131.8,128.7,128.4,127.8,127.1,126.5,53.0,45.1,38.3,30.1,11.8.

[0168] The structure of the product is inferred based on the above data:

[0169]

[0170] Example 16

[0171] Under air, 0.24 mmol of phenyldioxazolone, 0.2 mmol of phenylboronic acid, 0.3 mmol of trans-3-hexenoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver trifluoromethanesulfonate, 0.1 mmol of sodium carbonate, and 1.0 ml of tetrahydrofuran were added sequentially to a reaction vessel. After stirring at room temperature for 24 hours, the reaction solution was washed with saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography using a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 80:20:1 as the eluent. The desired product was not obtained.

[0172] Example 17

[0173] Under air atmosphere, 0.3 mmol of phenyldioxazolone, 0.2 mmol of phenylboronic acid, 0.3 mmol of trans-3-hexenoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver trifluoroacetate, 0.1 mmol of cesium acetate, and 1.0 ml of hexafluoroisopropanol were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 50:20:1, with a yield of 10%.

[0174] The structural characterization data of the obtained product are as follows:

[0175] 1 H NMR(500MHz,Chloroform-d)δ7.53(d,J=7.5Hz,2H),7.45(t,J=7.5Hz,1H),7.34(q,J=7.5Hz,4H),7.23(t,J=9.0Hz,3H),6 .34(d,J=9.0Hz,1H),4.77(m,1H),2.91(m,1H),2.70(m,1H),2.61(m,1H),1.88(m,1H),1.74(m,1H),0.83(t,J=7.5Hz,3H).

[0176] 13 C NMR (126MHz, Chloroform-d) δ175.2,167.3,140.1,134.2,131.6,128.7,128.63,128.59,127.2,126.8,50.9,49.9,37.9,25.2,12.1.

[0177] The structure of the product is inferred based on the above data:

[0178]

[0179] Example 18

[0180] Under air atmosphere, 0.3 mmol of phenyldioxazolone, 0.2 mmol of phenylboronic acid, 0.3 mmol of trans-3-hexenoic acid, 0.002 mmol of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer, 0.02 mmol of silver trifluoroacetate, 0.1 mmol of lithium carbonate, and 1.0 ml of hexafluoroisopropanol were added sequentially to a reaction vessel. After stirring at room temperature for 24 h, the reaction solution was washed with a saturated sodium chloride solution and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate:formic acid in a volume ratio of 50:20:1, with a yield of 50%.

[0181] The structural characterization data of the obtained product are as follows:

[0182] 1 H NMR(500MHz,Chloroform-d)δ7.53(d,J=7.5Hz,2H),7.45(t,J=7.5Hz,1H),7.34(q,J=7.5Hz,4H),7.23(t,J=9.0Hz,3H),6 .34(d,J=9.0Hz,1H),4.77(m,1H),2.91(m,1H),2.70(m,1H),2.61(m,1H),1.88(m,1H),1.74(m,1H),0.83(t,J=7.5Hz,3H).

[0183] 13 C NMR (126MHz, Chloroform-d) δ175.2,167.3,140.1,134.2,131.6,128.7,128.63,128.59,127.2,126.8,50.9,49.9,37.9,25.2,12.1.

[0184] The structure of the product is inferred based on the above data:

[0185]

Claims

1. A method for synthesizing α-amino acid and / or β-amino acid derivatives, characterized in that: The steps include: In an air atmosphere, with an organic solvent as a reaction medium, a carboxylic acid compound, a dioxazolone compound and an organic boronic acid react in the presence of a catalyst, a silver salt and a basic compound to obtain an α-amino acid and / or β-amino acid derivative; The carboxylic acid compound is where R 1 is hydrogen, benzyl, alkyl, substituted alkyl; the alkyl includes methyl, ethyl, propyl, isopropyl; the substituted alkyl is chloropentyl; the R 2 is methyl, ethyl or propyl; The organic boronic acid is 4-Dibenzofuranboronic acid R 3 is hydrogen, methyl, methoxy, fluorine, chlorine, bromine, trifluoromethoxy, furyl; R 4 is hydrogen, methyl, acetyl, trifluoromethyl, methoxy, nitro, fluorine, chlorine, or bromine; R 5 is hydrogen, methoxy, trifluoromethoxy, phenyl, trifluoromethyl, vinyl, fluorine, chlorine, bromine, iodine, ester, acetoxy, amide, or cyano; R 6 is hydrogen, methyl, methoxy, fluorine, or bromine; X is F, Cl, Br, or I; The dioxazolone compound is The R 7 is a substituted or unsubstituted aryl or alkyl group; The catalyst is a rhodium or ruthenium catalyst, specifically one or more of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer and p-cymene dichlororuthenium(II) dimer; The organic solvent is one or more of tetrahydrofuran, 1,4-dioxane, hexafluoroisopropanol, trifluoroethanol, toluene, dichloromethane, dichloroethane, acetone, and N,N-dimethylformamide.

2. The method for synthesizing α-amino acid and / or β-amino acid derivatives according to claim 1, characterized in that: R 5 wherein the ester group is -COOCH3; the amide group is -CON(R')(R"), R' and R" are methyl groups; R 7 wherein the substituted or unsubstituted aryl group is phenyl, 4-chlorophenyl, 3-fluorophenyl, 4-methoxyphenyl, or 2-thienyl; the alkyl group is C 1-6 alkyl.

3. The method for synthesizing α-amino acid and / or β-amino acid derivatives according to claim 1, characterized in that: The silver salt is one or more of silver carbonate, silver nitrate, silver benzoate, silver hexafluoroantimonate, silver trifluoroacetate, silver trifluoromethanesulfonate, silver acetate, and silver tetrafluoroborate; The alkaline compound is one or more of sodium acetate, copper acetate, cesium acetate, lithium acetate, potassium acetate, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium methoxide, and sodium benzoate; The organic solvent is one or more of tetrahydrofuran, 1,4-dioxane, dichloromethane, dichloroethane, and acetone, and the reaction yields an α-amino acid derivative; the organic solvent is one or more of hexafluoroisopropanol and trifluoroethanol, and the reaction yields a β-amino acid derivative.

4. The method for synthesizing α-amino acid and / or β-amino acid derivatives according to claim 3, characterized in that: The silver salt is one or more of silver carbonate and silver acetate; The alkaline compound is one or more of sodium carbonate and cesium acetate; The organic solvent is one or more of tetrahydrofuran and hexafluoroisopropanol.

5. The method for synthesizing α-amino acid and / or β-amino acid derivatives according to claim 4, characterized in that: When the organic solvent is tetrahydrofuran, the silver salt is silver carbonate, and the alkaline compound is sodium carbonate, the reaction produces an α-amino acid derivative; when the organic solvent is hexafluoroisopropanol, the silver salt is silver carbonate, and the alkaline compound is cesium acetate, a β-amino acid derivative is produced.

6. The method for synthesizing α-amino acid and / or β-amino acid derivatives according to claim 1, characterized in that: The molar ratio of the carboxylic acid compound, the organic boronic acid and the dioxazolone compound is (1-2): (1-2): (1-2); The molar ratio of the catalyst to the organic boronic acid is (0.005-0.02): 1; The molar ratio of the silver salt to the organic boronic acid is (0.05-0.6):1; The molar ratio of the basic compound to the organic boronic acid is (0.1-1):

1.

7. The method for synthesizing α-amino acid and / or β-amino acid derivatives according to claim 6, characterized in that: The molar ratio of the carboxylic acid compound, the organic boronic acid and the dioxazolone compound is (1.2-1.7):1:(1-1.7).

8. The method for synthesizing α-amino acid and / or β-amino acid derivatives according to claim 7, characterized in that: When obtaining α-amino acid derivatives, the molar ratio of the carboxylic acid compound, the organic boronic acid and the dioxazolone compound is (1.4-1.6):1:(1.1-1.3); when obtaining β-amino acid derivatives, the molar ratio of the carboxylic acid compound, the organic boronic acid and the dioxazolone compound is (1.4-1.6):1:(1.4-1.6).

9. The method for synthesizing α-amino acid and / or β-amino acid derivatives according to claim 4, characterized in that: The reaction temperature is room temperature and the reaction time is 20-28h; After the reaction is completed, subsequent treatment is performed, and the subsequent treatment refers to quenching the reaction, extracting with ethyl acetate, removing the solvent in the organic phase, and separating by column chromatography; the removal of the solvent in the organic phase refers to removing water in the organic phase and then removing the organic solvent; The quenching reaction refers to adding a saturated sodium chloride solution to the reaction system; the removal of water in the organic phase refers to drying with a desiccant, the desiccant being anhydrous sodium sulfate, and then filtering; the removal of the organic solvent in the organic phase refers to removing the organic solvent by distillation under reduced pressure; The eluent of the column chromatography is a mixed solvent of petroleum ether, ethyl acetate and formic acid, and the volume ratio of petroleum ether to ethyl acetate is (50-100):(15-40):

1.

10. The method for synthesizing α-amino acid and / or β-amino acid derivatives according to claim 4, characterized in that: Carboxylic acid compounds The general structural formula of the organic boronic acid is: 8 B(OH)2,R 8 Corresponding to the group in the organic boronic acid structure according to claim 1 or 2; The dioxazolone compound is The structure of the α-amino acid derivative is The structure of the β-amino acid derivative is

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