Method of chiral separation for D,L-phenylalanine ester or its salt

A phenylalanine ester, chiral resolution technology, applied in the preparation of D-type or L-type phenylalanine ester, the preparation of other chiral amino acid ester compounds, the preparation of chiral organic compounds, to reduce the The effect of production cost, low price and efficient splitting efficiency

Inactive Publication Date: 2007-02-28
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] So far, the method of preparing optically pure phenylalanine ester by chiral resolution using optically pure benzene ring acetic acid derivatives as a resolving agent has not been reported in the literature

Method used

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  • Method of chiral separation for D,L-phenylalanine ester or its salt
  • Method of chiral separation for D,L-phenylalanine ester or its salt
  • Method of chiral separation for D,L-phenylalanine ester or its salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] 18.5 grams (0.1mol) of D-alpha-methyl p-chlorophenylacetic acid and D, 17.9 grams (0.1mol) of L-phenylalanine methyl ester, in the water content of 200ml, be dissolved in the water-ethanol solution of 80%, The temperature was raised to 75°C to make the solution clear, and then the temperature was slowly lowered to 4°C to allow it to fully crystallize for 8 hours. The resulting white crystals were filtered, which was the crude product of D-α-methyl-p-chlorophenylacetic acid·L-phenylalanine methyl ester, and washed with 50% ethanol solution. This substance was recrystallized in an 80% water-ethanol solution to obtain 16.5 grams of refined salt of D-α-methyl p-chlorophenylacetic acid·L-phenylalanine methyl ester.

[0046] Dissolve 15 grams of D-α-methyl p-chlorophenylacetic acid·L-phenylalanine methyl ester refined salt in 100 ml of water-ethanol solution with a water content of 80%, and adjust the pH value to 2 with 3N hydrochloric acid solution. Ethanol was distilled of...

Embodiment 2

[0048] 18.5 g (0.1 mol) of L-α-methyl p-chlorophenylacetic acid and 17.9 g (0.1 mol) of partially racemic D, L-phenylalanine methyl ester, the optical purity (% o.p.) is expressed as D-benzene Alanine methyl ester is calculated as 65%, dissolved in 150ml of methanol solution, heated to 70°C to make the solution clear, and then slowly cooled to 4°C to allow it to fully crystallize for 8 hours. The resulting white crystals were filtered, which was the crude product of L-α-methyl-p-chlorophenylacetic acid·D-phenylalanine methyl ester, and washed with 50% methanol solution. This substance was recrystallized in a water-methanol solution with a water content of 80%, to obtain 26.3 grams of refined salt of L-α-methyl p-chlorophenylacetic acid·D-phenylalanine methyl ester.

[0049] Dissolve 15 grams of L-α-methyl p-chlorophenylacetic acid·D-phenylalanine methyl ester refined salt in 80 ml of methanol solution, and then add 15 ml of 3N sulfuric acid solution. And cooling down to 4°C, ...

Embodiment 3

[0051] According to the method of Example 1, D, L-phenylalanine ethyl ester can be salified with D-α-methyl p-chlorophenylacetic acid to form white D-α-methyl p-chlorophenylacetic acid L-phenylalanine Ethyl double salt. Then the method for processing double salt by embodiment 1 can obtain L-phenylalanine ethyl ester hydrochloride.

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Abstract

A chiral decomposing process of D,L-phenylalanine ester or its salt includes such steps as proportionally mixing D,L-phenylalanine ester with optical-purity aromatic acetic acid derivative, dissolving in solvent, heating, cooling to obtain the composite salt of aromatic organic acid and phenylalanine ester, recrystallizing, acidolyzing or alkali hydrolyzing, and extracting in organic solvent or separating by ion exchange risin to obtain optical-purity phenylalanine ester or phenylalanine.

Description

1. Technical field [0001] The invention belongs to the technical field of chemical separation of chiral compounds. Specifically, it relates to a preparation method of a chiral organic compound, especially a method for preparing D-type or L-type phenylalanine ester, which is also applicable to the preparation of other chiral amino acid ester compounds. 2. Technical Background [0002] Optically active phenylalanine esters are important pharmaceutical and food chemical intermediates. In recent years, the development and application of amino acid anticancer drugs and nutritional health products have promoted the production and development of optically pure phenylalanine esters. [0003] Optically pure phenylalanine ester is widely used in the fields of medicine, food and pesticides. In the synthesis of peptides, the esterification of phenylalanine is an important step in the protection and activation of amino acids, which can greatly improve the activity and selectivity of es...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C269/08C07C271/08
Inventor 焦庆才刘毅李加友钱绍松陈群贾晓娟郭丽芸
Owner NANJING UNIV
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