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Method for synthesis of tyrosine derivative

A synthesis method and tyrosine technology are applied in the preparation of organic compounds, chemical instruments and methods, preparation of carboxylic acid amides, etc., which can solve the problem of low purity of the synthesis method and achieve the effect of good product quality.

Inactive Publication Date: 2012-09-12
SHANGHAI JUNJIE BIOCHEM TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Mainly solve the technical problem of low purity in existing synthetic methods

Method used

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  • Method for synthesis of tyrosine derivative
  • Method for synthesis of tyrosine derivative
  • Method for synthesis of tyrosine derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0022] O , N-（2- benzene Preparation of formyl)-L--tyrosine:

[0023] In a 1000ml four-necked reaction flask, add 500ml of purified water, 20g of sodium hydroxide, control the temperature to 20°C, add 20g of L-tyrosine, 35g of benzoyl chloride, control the temperature to 50°C, stir for 60 minutes, add acetone dropwise 200ml, stirred for 1 hour, cooled to 5°C, and 16g of concentrated hydrochloric acid was added dropwise. Stir for 1 hour, centrifuge, wash with 50ml of purified water to obtain about 90g of O,N-(2-benzoyl)-L--tyrosine wet product, and vacuum dry at 80°C for 10 hours to obtain dry O,N-(2 -Benzoyl)-L-tyrosine 41g (content 99%, K.F: 0.5%).

Embodiment 2

[0025] O , N-（2- benzene Preparation of formyl)-L--tyrosine:

[0026] In a 1000ml four-necked reaction flask, add 500ml of purified water, 28g of potassium hydroxide, control the temperature to 10°C, add 20g of L-tyrosine, 35g of benzoyl chloride, control the temperature to 40°C, stir for 60 minutes, add acetone dropwise 200ml, stirred for 1 hour, cooled to 5°C, and 16g of concentrated hydrochloric acid was added dropwise. Stir for 1 hour, centrifuge, wash with 50ml of purified water to obtain about 90g of O,N-(2-benzoyl)-L--tyrosine wet product, and vacuum dry at 80°C for 10 hours to obtain dry O,N-(2 -Benzoyl)-L-tyrosine 41.5g (content 99.1%, K.F: 0.4%).

Embodiment 3

[0028] Preparation of N-benzoyl-L-tyrosyl di-n-propylamine:

[0029] Add 300ml of ethyl acetate to a 1000ml four-necked bottle, cool down to 0°C, add 40g of O,N-(2-benzoyl)-L-tyrosine, dropwise add 22g of triethylamine, and stir for 30 minutes; 25g of ethyl chloroformate, stirred at 30°C for 30 minutes, added 33g of dipropylamine, raised the temperature to 40°C and stirred for 30 minutes, added 5g of concentrated hydrochloric acid and 100ml of water, stirred for 15 minutes, separated into layers, removed the water layer, added 30g of sodium chloride and 100ml of purified water, separate layers, remove the water layer, distill the organic layer under reduced pressure at 40°C until solids are precipitated and cool down to 0°C, add 300ml of methanol, 5g of sodium hydroxide, stir at 0°C for 1 hour, and use 30g of concentrated hydrochloric acid and 100ml of purified water Adjust pH=1.0~2.0, stir at 0°C for 1 hour. After centrifugation, 30 ml of purified water and 30 ml of methan...

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Abstract

The invention discloses a method for synthesis of a tyrosine derivative. The method is a novel method for preparing the tyrosine derivative N-benzoyl-L-tyrosyl-di-n-propylamine. The method mainly solves the problem that the existing synthesis method has a low yield and low product purity. The method realizes the preparation of N-benzoyl-L-tyrosyl-di-n-propylamine by a two-step synthesis technology and comprises the following steps that 1, raw materials of L-tyrosine and benzoyl chloride undergo a reaction in the presence of an inorganic alkali aqueous solution and O,N-(2-benzoyl)-L-tyrosine crystallizes in an acetone aqueous solution; 2, the O,N-(2-benzoyl)-L-tyrosine, triethylamine, ethyl chloroformate and isopropamide are synthesized into O,N-(2-benzoyl)-L-tyrosyl-diisopropylamine in the presence of ethyl acetate; and 3, the O,N-(2-benzoyl)-L-tyrosyl-diisopropylamine is subjected to ethyl acetate extraction and condensation; then benzoyl of an oxy group is removed in an alcohol under alkaline conditions; and acidity adjustment is carried out in an alcohol aqueous solution so that N-benzoyl-L-tyrosyl-di-n-propylamine is obtained. The method is mainly used for preparation of an intermediate of a drug tiropramide hydrochloride from tyrosine as an initial raw material.

Description

technical field [0001] The present invention relates to a method for synthesizing tyrosine derivatives, in particular to a method for synthesizing N-benzoyl-L-tyrosyl di-n-propylamine, which is mainly used to manufacture drug hydrochloric acid with tyrosine as a starting material Intermediate of tiromide. Background technique [0002] The tyrosine derivative N-benzoyl-L-tyrosyl di-n-propylamine is a key intermediate in the synthesis of tiromide hydrochloride. Due to its complex structure, it has been successfully realized after years of technological development and technological progress. Industrial production. The chemical structural formula of N-benzoyl-L-tyrosyl di-n-propylamine is shown in formula I [0003] [0004] However, there are very few literature reports on N-benzoyl-L-tyrosyl di-n-propylamine, and the yield and purity are not high. Contents of the invention [0005] The object of the present invention is to provide a method for synthesizing good-qualit...

Claims

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Application Information

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IPC IPC(8): C07C237/22C07C231/12
Inventor 陈舒明
Owner SHANGHAI JUNJIE BIOCHEM TECH
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