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Method for preparing L-2-aminobutyric acid by asymmetric conversion method

A technology of aminobutyric acid and DL-2-, which is applied in the field of biochemistry to achieve the effects of reducing production costs, high yields, and reducing usage

Inactive Publication Date: 2011-05-18
NANJING INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Yet, can only obtain 50% L-2-aminobutyric acid theoretically by this method, and actual total yield only has about 30%

Method used

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  • Method for preparing L-2-aminobutyric acid by asymmetric conversion method
  • Method for preparing L-2-aminobutyric acid by asymmetric conversion method
  • Method for preparing L-2-aminobutyric acid by asymmetric conversion method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add a mixture of 20.6g (0.2mol) DL-2-aminobutyric acid and 15.1g (0.1mol) D-tartaric acid to 375ml of propionic acid, add 0.7g of benzaldehyde, react at 100°C for 6 hours, and cool to room temperature Immediately afterwards, cool with an ice-water bath for 0.5 hours, filter, and the mother liquor can be recycled, and the solid obtained by filtering is dissolved in water, and recrystallized to obtain 32.3 g of L-2-aminobutyric acid D-tartaric acid L-2-aminobutyrate, as 90.5% of theoretical yield.

Embodiment 2

[0027] Add a mixture of 30.9g (0.3mol) DL-2-aminobutyric acid and 15.1g (0.1mol) D-tartaric acid into 400ml of dilute hydrochloric acid, add 2.2g of methylbenzaldehyde, and react at 90°C for 8 hours. After cooling to room temperature, cool in an ice-water bath for 0.5 hour, filter, and the mother liquor can be recycled. The solid was dissolved in water and recrystallized to obtain 34.2 g of L-2-aminobutyric acid·D-tartaric acid·L-2-aminobutyric acid salt, which was 95.8% of the theoretical yield.

Embodiment 3

[0029] Add a mixture of 20.6g (0.2mol) DL-2-aminobutyric acid and 15.1g (0.1mol) D-tartaric acid into 375ml of acetic acid, add 0.7g of 2-hydroxynaphthaldehyde, react at 70°C for 6 hours, and cool After reaching room temperature, cool in an ice-water bath for 0.5 hour, filter, and the mother liquor can be recycled. The solid was dissolved in water and recrystallized to obtain 32.1 g of L-2-aminobutyric acid·D-tartaric acid·L-2-aminobutyric acid salt, which was 89.9% of the theoretical yield.

[0030] Preparation of L-2-aminobutyric acid from L-2-aminobutyric acid·D-tartaric acid·L-2-aminobutyric acid salt

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Abstract

The invention discloses a method for preparing L-2-aminobutyric acid by an asymmetric conversion method. The method comprises the following steps: mixing DL-2-aminobutyric acid with D-tartaric acid; in the presence of aromatic aldehyde as catalyst, reacting in acid solvent; cooling, filtering, and re-crystallizing to obtain a reaction intermediate product; mixing the reaction intermediate product with an aminolysis agent to be subjected to aminolysis reaction; and then cooling, filtering and washing to obtain the L-2-aminobutyric acid. The L-2-aminobutyric acid prepared by the method has the advantages of high yield, higher optical purity and chemical purity, lower cost and suitability for large-batch industrial production.

Description

technical field [0001] The invention belongs to the field of biochemistry, and in particular relates to a preparation method of chiral amino acid, especially a method for preparing L-2-aminobutyric acid from DL-2-aminobutyric acid. Background technique [0002] L-2-aminobutyric acid is an important chiral amino acid with a wide range of uses. It is an important raw material for the synthesis of levetiracetam and an important intermediate for the synthesis of other drugs. At present, L-2-aminobutyric acid Most of the production of DL-2-aminobutyric acid is prepared by synthetic methods, and then obtained by resolution. Therefore, the resolution of DL-2-aminobutyric acid is an important step in the production process of L-2-aminobutyric acid. [0003] At present, the resolution method of DL-2-aminobutyric acid with the most economic value is chemical resolution, that is, DL-2-aminobutyric acid reacts with chiral organic acids to form diastereomers, and utilizes diastereomer p...

Claims

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Application Information

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IPC IPC(8): C07C229/08C07C227/34
Inventor 韩冰徐良熊林张淼焱
Owner NANJING INST OF TECH
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