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A kind of new preparation method of carnosine

A new method and carnosine technology, applied in the field of preparation of dipeptides, can solve the problems of large-scale use and promotion of unfavorable products, expensive protective agents, low total yield, etc., and achieve sufficient supply, lower production costs, and reaction selectivity. Good results

Active Publication Date: 2015-11-18
ZHEJIANG GENEBEST PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The current main synthesis method of carnosine is mainly to react with histidine after amino protection and carboxyl activation of β-alanine, and then take off the protecting group to obtain the product carnosine. There are also many methods according to different protecting groups, such as literature (J.Org.Chem., 1964,229,1968-1970.) (J.Am.Chem.Soc., 1953,75,2388-2390.) etc. described, but some protective agents of this type of method are expensive, And the overall route steps are longer, which directly leads to lower total yield and higher cost, which is not conducive to large-scale use and promotion of products

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] A. Preparation of 1,3-oxazinane-2,6-dione (Ⅱ)

[0022] Add β-alanine (89g, 1.0mol) and anhydrous tetrahydrofuran (890g) into the reactor, stir well and then dropwise add anhydrous tetrahydrofuran solution of solid phosgene at room temperature (from 121g solid phosgene and 890g Anhydrous tetrahydrofuran configuration), after the dropwise addition, continue to stir the reaction at room temperature for 12 hours, after the reaction, remove most of the solvent tetrahydrofuran under reduced pressure, the residue is dissolved in ethyl acetate (178g), and the ethyl acetate layer is passed through 5% sodium bicarbonate solution, washed with water, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and the solvent ethyl acetate was removed by distillation to obtain a residue of 1,3-oxazinane-2,6-dione (II) The crude product is 108.4g, and the yield is about 94.2%. The crude product was directly used in the next reaction without further purification. The det...

Embodiment 2

[0028] Other steps are the same as in Example 1, except that the preparation method of 1,3-oxazinane-2,6-dione (II) in step A is as follows:

[0029] Add β-alanine (89g, 1.0mol) and anhydrous tetrahydrofuran (450g) into the reactor, stir well and then add dropwise anhydrous tetrahydrofuran solution of solid phosgene at room temperature (from 101g solid phosgene and 450g Anhydrous tetrahydrofuran configuration), after the dropwise addition, continue to stir the reaction at room temperature for 8 hours, after the reaction, remove most of the solvent tetrahydrofuran under reduced pressure, the residue is dissolved in ethyl acetate (178g), and the ethyl acetate layer is passed through 5% sodium bicarbonate solution, washed with water, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and the solvent ethyl acetate was removed by distillation to obtain a residue of 1,3-oxazinane-2,6-dione (II) The crude product is 92.6g, and the yield is about 80.5%. The crude ...

Embodiment 3

[0031] Other steps are the same as in Example 1, except that the preparation method of 1,3-oxazinane-2,6-dione (II) in step A is as follows:

[0032] Add β-alanine (89g, 1.0mol) and anhydrous tetrahydrofuran (750g) into the reactor, stir well and then dropwise add anhydrous tetrahydrofuran solution of solid phosgene at room temperature (from 110g solid phosgene and 750g Anhydrous tetrahydrofuran configuration), after the dropwise addition, continue to stir the reaction at room temperature for 10 hours, after the reaction, remove most of the solvent tetrahydrofuran under reduced pressure, the residue is dissolved in ethyl acetate (178g), and the ethyl acetate layer is passed through 5% sodium bicarbonate solution, washed with water, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and the solvent ethyl acetate was removed by distillation to obtain a residue of 1,3-oxazinane-2,6-dione (II) The crude product is 100.9g, and the yield is about 87.7%. The crud...

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PUM

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Abstract

The invention relates to a new preparation method of carnosine and relates to a preparation method of dipeptide consisting of beta-alanine and L-histidine. The method comprises the following steps: carrying out phosgene reaction between beta-alanine serving as a raw material and solids to form a ring, and then carrying out a ring opening reaction with L-histidine to obtain the target product. A new synthesis route is provided, the source of the used raw materials is wide and sufficient, the price of the raw materials is cheap, the product generated through reaction has high purity, good color and strong market competiveness.

Description

technical field [0001] The invention relates to a preparation method of carnosine, in particular to a preparation method of a dipeptide composed of two amino acids, beta-alanine and L-histidine. Background technique [0002] Carnosine was first discovered in 1900 by Russian chemist Gurevich. As an important dipeptide, it is mainly composed of two amino acids, β-alanine and L-histidine. [0003] Studies in the UK, South Korea, Russia and other countries have shown that carnosine has a strong antioxidant capacity and is beneficial to the human body. Carnosine has been shown to scavenge reactive oxygen species (ROS) and α-β-unsaturated aldehydes formed during oxidative stress by excessive oxidation of fatty acids in cell membranes. [0004] At the same time, carnosine can enhance the Hayflick limit of human fibroblasts and the rate of telomere shortening. The maintenance of telomeres may be beneficial to the growth of some potential cancers, so carnosine is also regarded as a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/64
CPCC07D233/64
Inventor 宋苗根
Owner ZHEJIANG GENEBEST PHARMA