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Method for producing optically active pyrrolidone carboxylic acid or alkali metal salt thereof

A technology of pyrrolidone carboxylic acid and zinc pyrrolidone carboxylic acid, which is applied in the field of manufacturing optically active pyrrolidone carboxylic acid or its alkali metal salt, can solve the problems of reducing and unknown production of pyrrolidone carboxylic acid, etc., and achieve the effect of simple yield

Pending Publication Date: 2020-03-17
AJINOMOTO CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no known method for producing pyrrolidonecarboxylic acid in a simple and high yield by removing zinc from the product without impairing the optical purity.
In such a case, it is known to use an ion exchange resin to remove zinc, but it is difficult to reduce it to about tens of ppm
[0008] As mentioned above, there is no known method of producing pyrrolidone carboxylic acid or its salt with high optical purity and high chemical purity (HPLC purity)

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0062] Hereinafter, the present invention will be described in more detail using examples, but these examples do not limit the present invention.

[0063] [Evaluation of chemical purity of optically active pyrrolidone carboxylic acid or its alkali metal salt (described as HPLC purity)]

[0064] The sample obtained after synthesis was analyzed by HPLC, and the ratio of the peak area of ​​the pyrrolidone carboxylic acid to the total area was taken as the HPLC purity.

[0065] HPLC analysis conditions

[0066] Column: Inertsil ODS-3 5μm, 250×4.6mm I.D.

[0067] Eluent: 30 mM sodium dihydrogen phosphate (pH 3.0)

[0068] Measurement temperature: 40℃

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Abstract

Provided is a method with which it is possible to produce, easily and at excellent yield, a pyrrolidone carboxylic acid of extremely high chemical purity and optical purity or an alkali metal salt thereof. A method for producing an optically active pyrrolidone carboxylic acid or an alkali metal salt thereof, the method including a step for adding an alkali metal hydroxide to a solution of optically active zinc pyrrolidone carboxylate dihydrate and filtering out a precipitate.

Description

technical field [0001] The present invention relates to a method for producing an optically active pyrrolidone carboxylic acid or an alkali metal salt thereof. Background technique [0002] Pyrrolidone carboxylic acid (PCA) is a compound useful not only as a cosmetic raw material but also as a raw material for pharmaceuticals and the like. Pyrrolidone carboxylic acid is synthesized by heating glutamic acid to undergo a self-cyclization reaction. As a production method, a solvent-free direct heating method, a high-pressure high-heat method in the presence of a solvent, a subcritical pressure heating method, and an enzymatic cyclization method (enzymatic cyclization method) are known. [0003] Japanese Patent Application Laid-Open No. 1-132560 (Patent Document 1) describes a solvent-free direct heating method. In the solvent-free direct heating method, the monovalent alkaline earth metal salt of glutamic acid in a solid state is heated to a temperature between 120° C. and 25...

Claims

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Application Information

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IPC IPC(8): C07D207/28
CPCC07D207/28
Inventor 杉本贵谦
Owner AJINOMOTO CO INC
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