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Method for chemical synthesis of N-[1 (1)-carbethoxy-3-hydro cinnamyl]-L-ulamine -N- carboxylic anhydride

A technology of ethoxycarbonyl and chemical synthesis, applied in the direction of organic chemistry and the like, can solve the problems of long reaction time of the synthesis method, increase the production cost, potential safety hazards, etc., and achieve the effects of eliminating potential production safety hazards, reducing the production of three wastes, and reducing the amount of consumption.

Active Publication Date: 2005-05-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

On the one hand, it causes greater environmental pollution and increases production costs; on the other hand, it brings great safety hazards to production, and the existing synthetic methods have a long reaction time

Method used

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  • Method for chemical synthesis of N-[1 (1)-carbethoxy-3-hydro cinnamyl]-L-ulamine -N- carboxylic anhydride
  • Method for chemical synthesis of N-[1 (1)-carbethoxy-3-hydro cinnamyl]-L-ulamine -N- carboxylic anhydride
  • Method for chemical synthesis of N-[1 (1)-carbethoxy-3-hydro cinnamyl]-L-ulamine -N- carboxylic anhydride

Examples

Experimental program
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Effect test

Embodiment 1

[0027] The feeding molar ratio is: N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine:bis(trichloromethyl)carbonate:catalyst=1:0.3 5:0.001, organic The solvent is dichloromethane, the amount of which is 15 times the mass of N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine, and the catalyst is tetrabutylurea.

[0028] In a 150 ml three-necked flask equipped with a thermometer, a reflux condenser, a constant pressure dropping funnel and magnetic stirring, add N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine ( 5.58 g) and an organic solvent, started stirring, cooled to -5° C. in an ice-salt bath, and then added bis(trichloromethyl)carbonate (2.1 g) and catalyst tetrabutylurea under ice-salt bath cooling. After the addition, continue to stir for 10 minutes under ice-salt bath cooling, then remove the ice-salt bath, stir at room temperature for 30 minutes, then warm up to 40°C, and continue to react for 18 hours with stirring at 40°C. After the reaction was over, the solvent was rec...

Embodiment 2

[0030] The molar ratio of feeding is: N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine:bis(trichloromethyl)carbonate:catalyst=1:0.5:0.001, organic solvent Dichloromethane is used in an amount of 15 times the mass of N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine, and the catalyst is tetrabutylurea. The amount of N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine weighed was 5.58 grams.

[0031] Other conditions and preparation steps were the same as in Example 1, and 6.0 grams of white N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine-N-carboxylic anhydride crystals were obtained, with a yield of 98.3% For, the detected content (HPLC) is 99.0%, and the melting point is 67.0-68.0°C, [α] D 25 =+11.8 (C=1, acetonitrile).

Embodiment 3

[0033] The molar ratio of feeding is: N-(1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine:bis(trichloromethyl)carbonate:catalyst=1:0.75:0.001, organic solvent Be dichloromethane, and its consumption is 15 times of N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine quality, and catalyst is tetrabutylurea. Weigh N-[1 The amount of (S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine was 5.58 g.

[0034] The preparation steps of other conditions were all the same as in Example 1, and 6.05 grams of white N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine-N-carboxylic anhydride crystals were obtained, and the yield was 99.1 %, the detected content (HPLC) is 99.2%, and the melting point is 67.1-67.8°C, [α] D 25 =+11.8 (C=1, acetonitrile).

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Abstract

The invention relates to a kind of chemosynthesis method of N-[1(S)-ethoxy carbonyl-3-phenyl propyl]-L-alanine-N-hydroxy acid anhydride, which is the medicine midbody for synthesizing Pulitzer series medicine such as Enalapril, Ramipril, Lisinopril and so on. The invention uses couple (trichloromethyl) ester carbonate and N-[1(S)-ethoxy carbonyl-3-phenyl propyl]-L-alanine as row material, and get the product by reacting with catalyst action in organic solvent. This chemosynthesis method is a manufacturing method of N-[1(S)-ethoxy carbonyl-3-phenyl propyl]-L-alanine-N-hydroxy acid anhydride, which has acquirable raw material, low production cost, and no three wastes normally.

Description

(1) Technical field [0001] The present invention relates to a kind of chemical synthesis method of N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine-N-carboxylic acid anhydride, especially using N-[1(S)- Ethoxycarbonyl-3-phenylpropyl]-L-alanine [N-(1(S)-ethyloxycarbonyl-3-phenylpropyl)-L-ananine] and bis(trichloromethyl) carbonate [bis(trichloro Methyl)carbonate] is a chemical synthesis method for preparing N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine-N-carboxylic acid anhydride by reacting raw materials in an organic solvent under the action of a catalyst. N-[1(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanine-N-carboxylic acid anhydride is mainly used in the synthesis of enalapril, ramipril, lisinopril, etc. series of drugs. (2) Technical background [0002] Before the present invention was made, the existing method of chemically synthesizing N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine-N-carboxylic acid anhydride was made by N-[1(S) -Ethoxycarbonyl-3-phenylpropyl]-L-a...

Claims

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Application Information

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IPC IPC(8): C07D263/44
Inventor 苏为科李永曙边高峰夏建胜谢媛媛梁现蕊
Owner ZHEJIANG UNIV OF TECH
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