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L-carnosine preparation method

A technology of carnosine and reaction, applied in the field of preparation of L-carnosine, can solve the problems of difficult large-scale production, few reaction steps, low yield, etc., and achieve the effect of reducing costs

Inactive Publication Date: 2013-11-27
ZHANG JIA GANG VINSCE BIO PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route has few reaction steps and no protective agent is needed, but the activity of ethyl cyanoacetate is not high, the yield is too low, only 35%, high temperature reaction, easy racemization
[0007] At present, although there are many routes for synthesizing L-carnosine, it is difficult to produce on a large scale and obtain good returns.

Method used

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  • L-carnosine preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Preparation of N-(N-BOC-propionyl)-L-histidine

[0018] Add 11-12Kg of L-histidine, 15.4Kg of N-BOC-β-alanine methyl ester hydrochloride and 80-100L of DMSO into the reactor, slowly add 5.2-6.5Kg of sodium ethoxide, and raise the temperature to 120-125°C. React for 5-6 hours, when the reaction is over, lower the temperature to 50°C, slowly add concentrated hydrochloric acid to adjust the pH to 2-3, then concentrate under reduced pressure to 12-15L, cool to room temperature, add 50-55L of acetone, stir in an ice bath, and precipitate coarse crystals , filtered to obtain a crude product with a weight yield of 30-32Kg.

Embodiment 2

[0020] Preparation of N-(N-BOC-propionyl)-L-histidine

[0021] Add 11-12Kg of L-histidine, 15.4Kg of N-BOC-β-alanine methyl ester hydrochloride and 80-100L of DMSO into the reactor, slowly add 1.9-2.1Kg of sodium hydride, and raise the temperature to 120-125°C. React for 5-6 hours, after the reaction is over, lower to room temperature, slowly add concentrated hydrochloric acid to adjust the pH to 2-3, then concentrate under reduced pressure to 12-15L, then cool to room temperature, add 50-55L of acetone, stir in an ice bath, and precipitate coarse crystals , filtered to obtain the crude product with a weight yield of 32-34Kg.

Embodiment 3

[0023] Preparation of L-carnosine

[0024] Add 30Kg of N-(N-BOC-propionyl)-L-histidine to the reaction kettle, add 60~70L of formic acid and stir to dissolve, 30L of 4mol / L hydrochloric acid / isopropanol solution, react at room temperature for 1.5~2.0h, use Dilute sodium bicarbonate to adjust the pH to 7-8, add 20-25L of ethanol, precipitate crystals, filter, wash with ether, and dry to obtain 26-29Kg of the product, with a total yield of 72-75%.

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Abstract

The present invention discloses an L-carnosine preparation method, which is characterized in that N-BOC-beta-alanine and L-histidine methyl ester hydrochloride are subjected to an aminolysis reaction under strong base catalysis, and the acid is subjected to deprotection to obtain the product, wherein the total yield of the two-step process is up to 72-75%. The preparation method has characteristics of significant process shortening, simple operation, high yield, good purity, low cost and the like, and is a process suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of L-carnosine. Background technique [0002] L-carnosine is composed of β-alanine and L-histidine. It is a natural active dipeptide, and generally only exists in mammalian body tissues, with a content of 0.1-0.3%. L-carnosine has a natural anti-oxidation effect, delays aging, and can also control blood sugar in the human body. At present, its derivative L-carnosine zinc has been listed as a new type of anti-ulcer drug. It can be seen that L-carnosine has excellent biological curative effect and has a large social demand, but pure natural L-carnosine cannot meet the market supply, so it is of great significance to research and develop chemically synthesized L-carnosine. [0003] At present, the chemical synthesis of L-carnosine mainly uses β-alanine and L-histidine as starting materials, and undergoes amino protection, carboxyl activati...

Claims

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Application Information

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IPC IPC(8): C07D233/64
Inventor 赵金召张梅彭学东王龙
Owner ZHANG JIA GANG VINSCE BIO PHARM
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