Method for preparing amino-acid ester

An amino acid ester and malonate technology, applied in the field of preparation of amino acid derivatives, can solve the problems of difficult industrialization, waste of halides, and high production costs, and achieve the effects of short reaction time, simple post-processing, and avoidance of waste.

Inactive Publication Date: 2014-05-14
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of amino acid esters by the nucleophilic substitution reaction of amines on halogenated esters will waste a lot of halides, the production cost is high and unsafe, and it is not easy to industrialize

Method used

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  • Method for preparing amino-acid ester
  • Method for preparing amino-acid ester
  • Method for preparing amino-acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] The reaction vials were loaded with TBAI (0.4 mmol, 148 mg), compound 1a (2 mmol, 214 mg), compound 3a (4 mmol, 472 mg), NaOAc (4 mmol, 164 mg), TBHP (0.6 mL), water (4.0 mL), acetonitrile (4.0 mL). Then the system was heated at 90°C in air for about 8 hours, quenched with saturated sodium sulfite solution, extracted with ethyl acetate (40 mL × 3), and the product was obtained by simple column chromatography 2a , the yield is 85%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

[0029] 1 H NMR (300 MHz, CDCl 3 ): δ 7.22 (t, J = 7.5 Hz, 2H), 6.73 (t, J = 7.5 Hz, 1H), 6.67 (d, J = 9.0 Hz, 2H), 4.04 (s, 2H), 3.68 (s, 3H), 3.03 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ): δ 171.0, 147.8, 131.8, 113.9, 109.4, 54.2, 52.0, 39.6; MS: Anal. Calcd. For C 10 h 14 NO 2 : 180, Found: 180 (M+1 + ); IR (KBr, cm -1 ): υ 1749.

Embodiment 2

[0031]

[0032] The reaction bottle is filled with I 2 (0.4 mmol, 102 mg), compound 1a (2 mmol, 214 mg), compound 3a(4 mmol, 472 mg), NaOAc (4 mmol, 164 mg), TBHP (0.6 mL), water (4.0 mL), acetonitrile (4.0 mL). Then the system was heated at 90°C in air for about 8 hours, quenched with saturated sodium sulfite solution, extracted with ethyl acetate (40 mL × 3), and the product was obtained by simple column chromatography 2a , the yield is 80%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

[0033] 1 H NMR (300 MHz, CDCl 3 ): δ 7.22 (t, J = 7.5 Hz, 2H), 6.73 (t, J = 7.5 Hz, 1H), 6.67 (d, J = 9.0 Hz, 2H), 4.04 (s, 2H), 3.68 (s, 3H), 3.03 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ): δ 171.0, 147.8, 131.8, 113.9, 109.4, 54.2, 52.0, 39.6; MS: Anal. Calcd. For C 10 h 14 NO 2 : 180, Found: 180 (M+1 + ); IR (KBr, cm -1 ): υ 1749.

Embodiment 3

[0035]

[0036] NIS (0.4 mmol, 90 mg), compound 1a (2 mmol, 214 mg), compound 3a (4 mmol, 472 mg), NaOAc (4 mmol, 164 mg), TBHP (0.6 mL), water (4.0 mL), acetonitrile (4.0 mL). Then the system was heated at 90°C in air for about 8 hours, quenched with saturated sodium sulfite solution, extracted with ethyl acetate (40 mL × 3), and the product was obtained by simple column chromatography 2a , the yield is 80%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

[0037] 1 H NMR (300 MHz, CDCl 3 ): δ 7.22 (t, J = 7.5 Hz, 2H), 6.73 (t, J = 7.5 Hz, 1H), 6.67 (d, J = 9.0 Hz, 2H), 4.04 (s, 2H), 3.68 (s, 3H), 3.03 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ): δ 171.0, 147.8, 131.8, 113.9, 109.4, 54.2, 52.0, 39.6; MS: Anal. Calcd. For C 10 h 14 NO 2 : 180, Found: 180 (M+1 + ); IR (KBr, cm -1 ): υ 1749.

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Abstract

The invention discloses a method for preparing amino-acid ester. In the presence of an oxidant, the method adopts an amine compound and malonic ester as reactants, an iodide as a catalyst and sodium acetate as alkali; a product amino-acid ester is prepared through nucleophilic substitution in a polar solvent; the general formula of the chemical structure of malonic ester is shown in the decstiption; and the iodide is one of I2, TBAI, NIS and IBr. According to the method disclosed by the invention, the reaction activity of the catalyst is high, the reaction conditions are moderate, the application range of substrate is wide, the aftertreatment is convenient, the yield of the target product is high, the preparation process is simple and green and environment-friendly, and the raw materials are widely available.

Description

technical field [0001] The invention belongs to the technical field of preparation of amino acid derivatives, and in particular relates to a catalytic preparation method of amino acid esters. Background technique [0002] Amino acid esters are a very important class of organic compounds, which are widely used in biology, medicine, pesticide, food, chemical industry and so on. For example: in the biological industry, amino acid esters protect the carboxyl groups in amino acids through esterification, which is extremely important in the application of amino acid and peptide chemistry; in the pharmaceutical industry, a variety of amino acid esters can be used directly or indirectly to treat different diseases diseases, and can also be used as intermediates of drugs; in the food industry, amino acid esters increase the solubility of amino acids and the specificity of enzyme catalysis, which can change the taste and flavor of food; in the chemical industry, amino acid esters can ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/08C07C229/18C07C233/47C07C231/12C07C233/83C07C269/06C07C271/22C07D215/06C07D213/74C07D295/15C07D333/16C07D307/42C07D277/82
Inventor 王璐万小兵张杰姜捷文时二波赵云
Owner SUZHOU UNIV
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