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Preparation method for benzyloxycarbonyl alanyl alanine

A technology of benzyloxycarbonylalanylalanine and benzyloxycarbonylalanylalanine methyl ester, which is applied in the field of preparation of dipeptides and can solve the problems that the synthesis method is not suitable for industrial production

Inactive Publication Date: 2013-05-01
GL BIOCHEM SHANGHAI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a preparation method of benzyloxycarbonylalanylalanine, which mainly solves the technical problem that the existing synthetic method is not suitable for industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0008] Alanine methyl ester hydrochloride is joined in methylene chloride, add methylamine, the amount of substance is 1 times of alanine methyl ester hydrochloride, add benzyloxycarbonyl alanine, the amount of substance is alanine 0.8 times that of methyl ester hydrochloride, ice bath, dropwise N , N' -dicyclohexylcarbodiimide in dichloromethane, with N , N' -The amount of dicyclohexylcarbodiimide is 1 times that of benzyloxycarbonylalanine, react overnight, filter off dicyclohexyl urea, remove dichloromethane by rotary evaporation, add ethyl acetate, and wash the organic layer with sodium bicarbonate solution , washed the organic layer with dilute hydrochloric acid, washed the organic layer with saturated brine, dried with ethyl acetate, filtered, and evaporated to dryness. The white solid was recrystallized to obtain benzyloxycarbonylalanylalanine methyl ester; Acylalanine methyl ester is dissolved in alcohol, adding sodium hydroxide solution, the amount of the substance...

Embodiment 2

[0013] Alanine methyl ester hydrochloride is joined in methylene chloride, sodium ethylate is added, the amount of substance is 1.3 times that of alanine methyl ester hydrochloride, benzyloxycarbonylalanine is added, and the amount of substance is alanine 1.2 times that of methyl ester hydrochloride, ice bath, dropwise N , N' -dicyclohexylcarbodiimide in dichloromethane, with N , N' - The amount of dicyclohexylcarbodiimide is 1.2 times that of benzyloxycarbonylalanine, react overnight, filter off dicyclohexyl urea, remove dichloromethane by rotary evaporation, add ethyl acetate, and wash the organic layer with sodium bicarbonate solution , washed the organic layer with dilute hydrochloric acid, washed the organic layer with saturated brine, dried with ethyl acetate, filtered, and evaporated to dryness. The white solid was recrystallized to obtain benzyloxycarbonylalanylalanine methyl ester; Acylalanine methyl ester is dissolved in alcohol, adding sodium hydroxide solution, ...

Embodiment 3

[0015] Alanine methyl ester hydrochloride is joined in methylene chloride, add butyllithium, the amount of substance is 1.1 times of alanine methyl ester hydrochloride, add benzyloxycarbonyl alanine, the amount of substance is alanine Amino acid methyl ester hydrochloride 1 times, ice bath, drop N , N' -dicyclohexylcarbodiimide in dichloromethane, with N , N' - The amount of dicyclohexylcarbodiimide is 1.1 times that of benzyloxycarbonylalanine, react overnight, filter off dicyclohexyl urea, remove methylene chloride by rotary evaporation, add ethyl acetate, and wash the organic layer with sodium bicarbonate solution , washed the organic layer with dilute hydrochloric acid, washed the organic layer with saturated brine, dried with ethyl acetate, filtered, and evaporated to dryness. The white solid was recrystallized to obtain benzyloxycarbonylalanylalanine methyl ester; Acylalanine methyl ester is dissolved in alcohol, and sodium hydroxide solution is added, the amount of w...

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Abstract

The invention relates to a preparation method for two peptides, in particular to the preparation method for benzyloxycarbonyl alanyl alanine, and mainly solves the technical problem that the conventional synthetic method is not suitable for industrial production. The invention adopts the following technical scheme: the preparation method comprises the steps as follows: 1, adding L-alanine methyl ester hydrochloride into dichloromethane, adding organic alkali and benzyloxycarbonyl alanine, carrying out ice-bath treatment, dropwise adding a dichloromethane solution of N,N'-dicyclohexyl carbodiimide, reacting overnight, filtering out dicyclohexylurea, rotationally steaming to remove dichloromethane, carrying out conventional treatment to obtain a white solid, and re-crystallizing to obtain benzyloxycarbonyl alanyl alanine methyl ester; and 2, dissolving benzyloxycarbonyl alanyl alanine methyl ester in alcohol, adding a sodium hydroxide solution for saponification reaction, and carrying out conventional treatment to obtain benzyloxycarbonyl alanyl alanine as a final product.

Description

technical field [0001] The invention relates to a preparation method of two peptides, in particular to a preparation method of benzyloxycarbonylalanylalanine. Background technique [0002] The synthesis of two peptides is the simplest among the simplest peptide synthesis. One molecule of carboxyl group is removed from one molecule of free amino group and one part of free carboxyl group. The synthesis of two peptides is especially suitable for liquid phase synthesis. Two peptides are synthesized from different amino acids There are different condensation methods. The book "Peptide Synthesis" published by Science Press in September 1985 introduced methods such as carbodiimide method, activated ester method, mixed anhydride method, azide method, and specific applications. To two different amino acids, it needs to be used flexibly. After searching, no preferred method for compounds with the same sequence was found. Benzyloxycarbonylalanylalanine is a commonly used polypeptide, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/062
Inventor 徐红岩李忠亮
Owner GL BIOCHEM SHANGHAI
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