A kind of preparation method of chiral phenyl lactic acid

A technology of phenyllactic acid and phenyllactate, which is applied in the preparation of carboxylate, the preparation of organic compounds, organic chemical methods, etc., can solve the problem of no biosynthesis method, difficulty in processing industrial waste, environmental pollution of dangerous processes, etc. problem, to achieve the effect of good splitting efficiency, cheap recycling, and easy recycling

Active Publication Date: 2021-02-26
上海予利生物科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The chemical synthesis method can carry out diazotization reaction through phenylalanine. The cost of raw materials is high, the reaction is a dangerous process and there is environmental pollution, and it is difficult to deal with a large amount of industrial waste.
The biological method, whether it is a fermentation method, a biocatalysis method or an enzymatic method, requires a lot of research work in the early stage, to find an ideal preparation method, and at the same time have a good separation and purification method. No industrialized biosynthesis method

Method used

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  • A kind of preparation method of chiral phenyl lactic acid

Examples

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Comparison scheme
Effect test

Embodiment 1

[0021] Synthesis of (S)-Phenylethylamine-D-Phenyl Lactate

[0022] Add 3.3 g of DL-phenyl lactic acid, 30 ml of ethyl acetate / methanol (volume ratio 2:1) mixture, add 1.5 g of (S)-phenylethylamine, heat properly until completely dissolved, cool to below room temperature, A solid was precipitated to obtain 1.5 g of a crude product of (S)-phenethylamine-D-phenyllactate with an optical rotation of +24° (C=1 ethanol).

Embodiment 2

[0024] Synthesis of (S)-Phenylethylamine-D-Phenyl Lactate

[0025] Add 3.3 g of DL-phenyllactic acid, 30 ml of ethyl acetate / ethanol (volume ratio 3:1) mixture, add 2.0 g of (S)-phenylethylamine, heat properly until completely dissolved, then cool to below room temperature, A solid was precipitated to obtain 1.6 g of a crude product of (S)-phenethylamine-D-phenyllactate with an optical rotation of +28° (C=1 ethanol).

Embodiment 3

[0027] Synthesis of (S)-Phenylethylamine-D-Phenyl Lactate

[0028] Add 3.3 g of DL-phenyl lactic acid, 20 ml of ethyl acetate / ethanol (volume ratio 4:1) mixture, add 2.4 g of (S)-phenylethylamine, heat properly until completely dissolved, then cool to below room temperature, A solid was precipitated to obtain 1.7 g of a crude product of (S)-phenethylamine-D-phenyllactate with an optical rotation of +30° (C=1 ethanol).

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Abstract

The invention relates to a preparation method of chiral phenyllactic acid. The preparation method comprises the steps: salifying (S)-phenethylamine serving as a resolving agent and DL-phenyllactic acid in a specific solvent, and carrying out recrystallization to obtain (S)-phenethylamine-D-phenyl lactate; salifying (R)-phenethylamine serving as a resolving agent and DL-phenyllactic acid in a specific solvent, and carrying out recrystallization to obtain (R)-phenethylamine-L-phenyl lactate; and carrying out acid dissociation to prepare the chiral phenyllactic acid. Compared with the prior art,the preparation method has the advantages that the adopted resolving agent is cheap, available and easy to recover, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for splitting chiral acids with chiral amines, in particular to a preparation method for splitting phenyl lactic acid. Background technique [0002] Phenyllactic acid (pHenyllactic acid, PLA), as one of the metabolites of lactic acid bacteria, widely exists in lactic acid bacteria fermentation products. A large number of studies have shown that phenyl lactic acid is a broad-spectrum antibacterial substance, which has a good inhibitory effect on most Gram-positive bacteria, negative bacteria and fungi, and its antibacterial activity is stronger than some commonly used food preservatives, such as benzene Sodium formate, potassium sorbate, etc. The second carbon atom of phenyl lactic acid is a chiral carbon atom, so there are two isomers of D- or L-type, which are D-phenyl lactic acid and L-phenyl lactic acid respectively, and the research found that D-phenyl lactic acid The inhibitory activity of phenyllactic acid agai...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/487C07C59/48
CPCC07B2200/07C07C51/487C07C59/48
Inventor 金健林张林宝严承飞
Owner 上海予利生物科技股份有限公司
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