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Method for preparing D-phenylalanine through asymmetric transformation of L-phenylalanine

A technology of phenylalanine and phenylalanine salt, which is applied in the directions of cyanide reaction preparation, chemical instruments and methods, preparation of organic compounds, etc., can solve problems such as difficulty in large-scale industrialization, high production cost, and difficulty in obtaining, To achieve the effect of reducing input and operating steps and processes, reducing production costs and improving production efficiency

Active Publication Date: 2015-09-23
CHENGDU LIKAI CHIRAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method needs to salt DL-phenylalanine first, and then add pyridine and the like to dissociate in situ when splitting, which increases the input of raw materials and increases the operation steps, and the racemic agent is Pyridine aldehyde, the production cost is high, is not suitable for industrial production, and the two-step conversion yield is only about 83% in the embodiment 1 of this patent; CN1226275C discloses taking DL-phenylalanine as raw material, taking D-tartaric acid as Resolving agent, using organic acid as solvent and aromatic aldehyde as racemization catalyst, through resolution, dissociation, separation and purification to obtain D-phenylalanine; (3) asymmetric catalytic method: for example, CN102234241 discloses a The method of chemical cooperation with D-phenylalanine, acetamido-D-phenylalanine is obtained by asymmetric reduction of acetylaminocinnamic acid and its derivatives in the presence of a chiral catalyst, and this compound is further hydrolyzed to obtain D-phenyl Alanine
[0004] The stereoselectivity of the biological method is good, but there are problems such as the stability and catalytic efficiency of the biocatalyst, and there are still difficulties in large-scale industrialization
In the wrong catalytic method, the chiral catalyst is not easy to obtain, the route is long, and the cost is high
The chemical resolution method is still the most used method in industry at present, but the classical resolution method only has a theoretical yield of 50%, while the actual total yield is only about 30%, and the optical purity is not high. cumbersome
Although the dynamic dynamic split developed later made up for the deficiencies of the classical split method to a certain extent, it still has problems such as stability, split efficiency, product quality, and production cost.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 66 g L-phenylalanine, 5 g n-butyraldehyde, 400 g propionic acid in turn to the reaction flask, then add 60 g D-tartaric acid solid, and heat up to 75-85 o C. Stir the reaction for 10 hours, stop heating, naturally cool to room temperature, filter, the filtrate can be recycled, the solid filter cake is washed with propionic acid, and dried to obtain white solid D-phenylalanine·D-tartrate. Add the salt obtained in batches to 65 g of 25% ammonia water, release heat, stir for 1-2 hours, drop to room temperature, filter, wash the filter cake with a small amount of water, and dry to obtain 60.5 g of D-phenylalanine with a yield of 91.6 %, 99.8% ee.

Embodiment 2

[0028] Add 66 g of L-phenylalanine, 4 g of propionaldehyde, and 660 g of acetic acid in turn to the reaction flask, then add 30 g of D-tartaric acid solid, and heat up to 60-75 o C. Stir the reaction for 5 hours, stop heating, naturally cool to room temperature, filter, the filtrate can be recycled, the solid filter cake is washed with ether, and dried to obtain white solid D-phenylalanine·D-tartrate. Add the salt obtained in batches to 80 g of 25% ammonia water, release heat, stir for 1-2 hours, drop to room temperature, filter, wash the filter cake with a small amount of water, and dry to obtain 59.8 g of D-phenylalanine, yield 90.7%, 99.5% ee.

Embodiment 3

[0030] Add 66 g L-phenylalanine, 3.5 g n-valeraldehyde, 300 g butyric acid successively to the reaction flask, then add 120 g D-tartaric acid solid, and heat up to 80-90 o C. Stir the reaction for 6 hours, stop heating, naturally cool to room temperature, filter, the filtrate can be recycled, the solid filter cake is washed with ethyl acetate, and dried to obtain white solid D-phenylalanine·D-tartrate. Add the salt obtained in batches to 100 g of 25% ammonia water, release heat, stir for 1-2 hours, drop to room temperature, filter, wash the filter cake with a small amount of water, and dry to obtain 59.4 g of D-phenylalanine, yield 90%, 99.6% ee.

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Abstract

The invention discloses a method for preparing D-phenylalanine through asymmetric transformation of L-phenylalanine, and belongs to the technical field of chirality organic compounds. The method comprises steps: dissolving the L-phenylalanine and aldehyde catalysts in organic acid, adding D-tartaric acid, performing a reaction for 5-10 hours at the temperature of 60-90 DEG C, performing cooling and filtration, and washing a solid with an organic solvent so as to obtain D-tartaric acid .D-phenylalanine salt; and adding the obtained D-tartaric acid .D-phenylalanine salt into alkali liquid in batches, performing dissociation, performing a stirring reaction for 1-2 hours, and performing filtration, washing and drying so as to obtain the D-phenylalanine. The method disclosed by the invention solves the problems of poor stability, low resolution efficiency, poor product quality, high production cost and the like existing in the technology of preparing the D-phenylalanine through the L-phenylalanine. The method disclosed by the invention has the advantages of being high in yield, low in production cost, simple to operate, easy in industrialization and the like.

Description

technical field [0001] The invention relates to the technical field of chiral organic compounds, in particular to a method for preparing D-phenylalanine through asymmetric conversion of L-phenylalanine. Background technique [0002] D-phenylalanine is an important chiral amino acid, which is widely used in the fields of medicine and chemical industry. For example, D-phenylalanine is the raw material of anti-diabetic drug nateglinide, anti-tumor drug octreotide, and anti-AIDS drug indinavir, and can also be used as a chiral reagent or sex intermediate. In addition, D-phenylalanine can also be used directly as a drug, such as an anti-stress agent, a preparation for controlling diabetes, an anti-inflammatory analgesic, etc., and can also be used as a chiral reagent or a chiral intermediate. [0003] At present, there are many reports on the preparation methods of D-phenylalanine, which are mainly divided into the following categories: (1) Biological methods, such as CN1026186...

Claims

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Application Information

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IPC IPC(8): C07C229/36C07C227/30C07C227/34
Inventor 袁伟成左健周鸣强徐小英张晓梅
Owner CHENGDU LIKAI CHIRAL TECH
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