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Method for preparing D-phenylalanine through dynamic kinetic resolution

A dynamic kinetics, phenylalanine technology, applied in chemical instruments and methods, preparation of cyanide reactions, preparation of organic compounds, etc., can solve the problems of large production-to-solubilization ratio, mild conditions, and long resolution time. , to achieve the effect of improving the split yield, stable product quality and reducing operating costs

Inactive Publication Date: 2011-04-13
SHANGHAI HUAYI GRP CO
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  • Abstract
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  • Claims
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Problems solved by technology

In this method, DL-phenylalanine is the resolution substrate, and the organic acid propionic acid is used as the solvent. The acidity in the system is relatively strong, the conditions are not mild, and the production-solvent ratio is very large, requiring more than 10 times Only the solvent can achieve the effect of dissolving the substrate, and the splitting time is longer, more than 6 hours

Method used

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  • Method for preparing D-phenylalanine through dynamic kinetic resolution
  • Method for preparing D-phenylalanine through dynamic kinetic resolution

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Embodiment 1

[0029] (1) Preparation of L-phenylalanine hydrochloride:

[0030] Add 99.1g (0.60mol) of L-phenylalanine and 241g of 10% (0.66mol) hydrochloric acid to a stirred reactor, stir at room temperature until the solids are completely dissolved, then evaporate the reaction solution to dryness to obtain phenylalanine salt Salt 121g.

[0031] (2) Preparation of D-phenylalanine L-DBTA di-salt:

[0032] In a reactor with stirring, heating and thermometer, 40.3g (0.20mol) of L-phenylalanine hydrochloride obtained in step (1) was dissolved in 82ml of methanol, and 2.5g (0.01mol) of 2- Aldehydpyridine, stirred and heated to 65°C. Begin to add dropwise the mixed solution that is made up of 35.8g (0.10mol) L-DBTA, 20.2g (0.2mol) triethylamine, 72ml methanol, along with the adding of mixed solution, D-phenylalanine·L-DBTA disalt It also crystallized gradually, and the mixed solution was added after 1.5 hours; reacted for another 30 minutes, and the system was cooled to room temperature, and...

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Abstract

The invention discloses a method for preparing D-phenylalanine through dynamic kinetic resolution. The method comprises the following steps of: reacting L-phenylalanine serving as raw materials with hydrochloric acid to generate L-phenylalanine hydrochloride; racemizing and resolving under the action of a solvent and a racemization catalyst by taking the L-phenylalanine hydrochloride as a substrate and dibenzoyl tartaric acid (L-DBTA) as a resolving agent to obtain D-phenylalanine.L-DBTA disalt; and finally performing triethylamine resolution to prepare the target product D-phenylalanine. Compared with the prior art, the method directly takes the L-phenylalanine as the resolving substrate, mild alcohol as the solvent and an aldehyde pyridine compound as the racemization catalyst, racemizes and resolves the L-phenylalanine into the D-phenylalanine.L-DBTA disalt, has a theoretical conversion rate of about 100 percent, greatly improves the resolution yield, reduces the operating cost, ensures stable product quality and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing D-phenylalanine through dynamic kinetic resolution. Background technique [0002] D-phenylalanine can be used for biochemical research, and can also be used as a pharmaceutical intermediate or raw material to synthesize nateglinide and other drugs for the treatment and prevention of osteoporosis, cardiovascular, diabetes, arteriosclerosis and other diseases. Its structural formula is: [0003] [0004] Existing literature discloses a kind of using DL-phenylalanine as raw material, D-tartaric acid as resolving agent, salicylaldehyde as catalyst, asymmetric transformation and resolution in propionic acid solvent to obtain D-phenylalanine [not yet Ben Mei, Jiang Lijian, Preparation of D-Phenylalanine by Asymmetric Transformation Resolution [J], Chinese Journal of Pharmaceutical Industry, 2007, 38(7): 475-476]. In this method, DL-phenylalanine is the resolution substrate, and the organic acid propionic a...

Claims

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Application Information

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IPC IPC(8): C07C229/36C07C227/34C07C227/36
Inventor 安国成顾慧娟廖本仁
Owner SHANGHAI HUAYI GRP CO
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