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Synthetic method of poly-substituted dimethyl amino phenyl acetic acid compound

A technology of dimethylaminophenyl and synthetic methods, which is applied in the field of organic compound synthesis, can solve the problems of complex operation, poor safety, and harm to skin and mucous membranes, and achieve the effects of good safety, mild reaction, and high product yield

Active Publication Date: 2020-10-16
苏州爱玛特生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In the above synthesis method, the toxic substance formaldehyde is used in the raw materials, which is irritating, harmful to skin and mucous membranes, and easy to cause cancer
Moreover, sodium cyanoborohydride, a highly flammable substance, is used, which is poor in safety. It needs to be mixed by shaking or ultrasonic to help dissolve, and the operation is complicated.

Method used

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  • Synthetic method of poly-substituted dimethyl amino phenyl acetic acid compound
  • Synthetic method of poly-substituted dimethyl amino phenyl acetic acid compound
  • Synthetic method of poly-substituted dimethyl amino phenyl acetic acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of 2-(4-(dimethylamino)phenyl)acetic acid

[0048]

[0049] The synthesis steps are: (1) add 2-(4-aminophenyl)acetic acid (4.53g, 30mmol), 25mL of anhydrous methanol, SOCl to a 100mL flask 2 (2.20mL, 30mmol), stirred at 60°C for 12h, cooled to room temperature, and removed the solvent by rotary evaporation to obtain intermediate 1 (methyl 2-(4-aminophenyl)acetate), which was carried out to the next step.

[0050](2) Under Ar protection conditions, add 2-(4-aminobenzene) methyl acetate (1.65g, 10mmol) and methyl p-toluenesulfonate (7.45g, 40mmol) in a 50mL flask, and add 2N KOH solution (30mL), heated to 80°C and stirred, quickly added tetrabutylammonium bromide (0.13g, 0.4mmol), reacted for 6h, cooled the reaction solution to room temperature, extracted with ether, combined the organic phases, and dried over anhydrous magnesium sulfate treatment, spin off most of the solvent, and purify by silica gel column chromatography, using ethyl acetate / petroleum eth...

Embodiment 2

[0054] Synthesis of 2-(4-(dimethylamino)-3-methylphenyl)acetic acid

[0055]

[0056] In this example, the specific preparation method is the same as in Example 1, except for the following conditions: in step (1), replace 2-(4-amino) with 2-(4-amino-3-methylphenyl)acetic acid (30mmol) phenyl) acetic acid, intermediate 2 is obtained; in step (2), intermediate 2 (10mmol) is taken to replace intermediate 1 (2-(4-aminobenzene) methyl acetate), and product 2-(4-( Dimethylamino)-3-methylphenyl)acetic acid, yield 80%.

[0057] Carry out NMR detection to product, the result is as follows:

[0058] 1 H NMR (400MHz,D 2 O) δ7.15(dt,1H),7.07(q,1H),6.76(d,1H),3.55(t,2H),2.84(s,6H),2.28(s,3H).

[0059] 13 C NMR (125MHz, DMSO) δ177.41(d), 148.99, 130.61(m), 129.03(d), 127.51(ddd), 116.00(d), 43.13, 40.92(dt), 17.97(d).

Embodiment 3

[0061] Synthesis of 2-(4-(dimethylamino)-2-methylphenyl)acetic acid

[0062]

[0063] In this example, the specific preparation method is the same as in Example 1, except for the following conditions: in step (1), replace 2-(4-amino) with 2-(4-amino-2-methylphenyl)acetic acid (30mmol) phenyl) acetic acid, intermediate 3 is obtained; in step (2), intermediate 3 (10mmol) is taken to replace intermediate 1 (2-(4-aminobenzene) methyl acetate), and product 2-(4-( Dimethylamino)-2-methylphenyl)acetic acid, yield 81%.

[0064] Carry out NMR detection to product, the result is as follows:

[0065] 1 H NMR (400MHz,D 2 O)δ7.14(dt,1H),6.71(m,2H),3.59(d,2H),2.95(s,6H),2.21(s,3H).

[0066] 13 C NMR (125MHz, DMSO) δ176.49(d), 151.13, 137.61(d), 130.00(m), 126.06(d), 114.89(q), 110.88(dd), 40.40, 40.10(dd), 19.43( d).

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Abstract

The invention relates to a synthesis method of a poly-substituted dimethyl amino phenyl acetic acid compound. The synthesis method comprises the following steps: carrying out methyl esterification reaction on a compound shown in a formula I to obtain a compound shown in a formula II; and enabling the compound shown in the formula II to react with a N-methylation reagent in the presence of a phasetransfer catalyst under an alkaline condition to obtain a compound shown as a formula III; wherein the formula I, the formula II, and the formula III are shown in the specification, in the formula I and the formula II, R1' is NH2, R2 is one of alkyl and H, R1' and R2 are respectively substituted at p-position, o-position and m-position on a benzene ring, and R1' and R2 are not simultaneously substituted at one position; and in the formula III, R1 is N(CH3)2, R2 is one of alkyl and H, R1 and R2 are respectively substituted at p-position, o-position and m-position on a benzene ring, and R1 and R2 are not simultaneously substituted at one position. In the synthesis process, the use of a highly flammable substance sodium cyanoborohydride is avoided, the safety is good, the reaction is mild, and the product yield is as high as 80% or above.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of multi-substituted dimethylaminophenylacetic acid compounds. Background technique [0002] Multi-substituted dimethylaminophenylacetic acid compounds are a class of amino acids that are important pharmaceutical intermediates and are widely used in the field of medicinal chemistry. For example, as an intermediate of compounds such as isotope derivatization reagents used to label a series of compounds with amino groups or phenolic hydroxyl groups. [0003] The synthesis method of this type of compound is relatively lacking. The currently published synthesis method of this type of amino acid compound is obtained by reacting formaldehyde and phenyl primary amine carboxylic acid under the condition of sodium cyanoborohydride, such as the synthesis method published in Chinese patent CN109111389 , the route is as follows: [0004] ...

Claims

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Application Information

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IPC IPC(8): C07C227/18C07C227/40C07C229/42
CPCC07C227/18C07C227/40C07C229/42Y02P20/55
Inventor 汪明中朱明新苏道李金金
Owner 苏州爱玛特生物科技有限公司
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