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Synthetic method of L-carnosine

A synthesis method and carnosine technology, applied in the field of L-carnosine synthesis, can solve the problems that the quality cannot meet people's daily requirements, are not suitable for industrial production, and have high solvent consumption, achieve difficult separation and reuse, mild reaction conditions, and reduce raw materials. The effect of consumption

Active Publication Date: 2008-10-15
SUZHOU FUSHILAI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The L-carnosine product yield that above synthetic method obtains is only 83%, and quality does not reach people's daily requirement, and solvent consumption is too high, causes environmental pollution, thereby also not suitable for suitability for suitability for industrialized production

Method used

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  • Synthetic method of L-carnosine
  • Synthetic method of L-carnosine
  • Synthetic method of L-carnosine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of phthaloyl-β-alanine (II).

[0019] In a 2000ml reaction flask, add 1000g toluene, 69.1g β-alanine (0.776mol), 114.9g phthalic anhydride (0.776mol) and 6.5g triethylamine (0.064mol), heat up to reflux, and separate the reaction For the generated moisture, when there is no obvious moisture in the water separator, the reaction is over, and the toluene is recovered under normal pressure. After a large amount of white solid appears, it is recovered under reduced pressure. The temperature of the material does not exceed 125 ° C. All dissolved, kept stirring for 15 min, then cooled to 10°C, filtered, and dried to obtain 167.5 g of product (II), with a yield of 98.5%, HPLC>99.5. The reaction formula of this embodiment is as follows, wherein (II) represents phthaloyl-β-alanine.

[0020]

Embodiment 2

[0022] Preparation of phthaloyl-β-alanine (II).

[0023] In a 2000ml reaction flask, add 1000g benzene, 69.1g β-alanine (0.776mol), 114.9g phthalic anhydride (0.776mol) and 6.5g triethylamine (0.064mol), heat up to reflux, and separate the reaction For the generated moisture, when there is no obvious moisture in the water separator, the reaction is over, and the toluene is recovered under normal pressure. After a large amount of white solid appears, it is recovered under reduced pressure. The temperature of the material does not exceed 125 ° C. All dissolved, kept stirring for 15 min, then cooled to 10°C, filtered, and dried to obtain 167 g of product (II), with a yield of 98.2%, HPLC>99.5.

[0024] The chemical reaction formula of this embodiment is the same as that of Embodiment 1.

Embodiment 3

[0026] Preparation of phthaloyl-β-alanine (II).

[0027] In a 2000ml reaction flask, add 1000g xylene, 69.1g β-alanine (0.776mol), 114.9g phthalic anhydride (0.776mol) and 6.5g triethylamine (0.064mol), heat up to reflux, separate The moisture generated by the reaction, when there is no obvious moisture in the water separator, the reaction is over, and the toluene is recovered under normal pressure. After a large amount of white solid appears, it is recovered under reduced pressure. The temperature of the material does not exceed 125°C, then add 800g of water, and heat to 90°C. All the solids were dissolved, kept stirring for 15 minutes, then cooled to 10°C, filtered, and dried to obtain 166.7 g of product (II), with a yield of 98%, HPLC>99.5. The chemical reaction formula of this embodiment is the same as that of Embodiment 1.

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Abstract

A method for synthesizing L-carnosine belongs to the organic synthesis technical field. The method is as follows: beta-alanine is dissolved in non-polar solvent to be reacted with phthalic anhydride under the catalysis of organic amine, and then phthaloyl-beta-alanine is obtained through water recrystallization; the phthaloyl-beta-alanine is dissolved in solvent to synthesize phthaloyl-beta-alanyl chloride through the chlorinated reagent of acyl chloride phthaloyl-beta-alanine; L-histidine is reacted with hexamethyl disilazane or trimethylchlorosilane to obtain L-histidine trimethylsilane protector; the protector is reacted with the phthaloyl-beta-alanyl chloride to obtain hydrochloride product with the protecting group divested by water, and then neutralization product is obtained by the hydrochloride product obtained through the neutralization condensation reaction of alkaline reagent, thereby obtaining L-carnosine crude product through the hydrazinolysis of the neutralization product by hydrazine hydrate; and the crude product is purified to obtain L-carnosine finished product. The method has low raw material consumption, short reaction procedure and high yield; moreover, the quality of synthesized L-carnosine can meet the requirements of industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of L-carnosine. [0002] The chemical name of L-carnosine is beta-alanyl-L-histidine. Its structural formula is as follows: [0003] Background technique [0004] Carnosine is a natural dipeptide that exists in the skeletal muscles and brains of vertebrates. Its chemical essence is formed by the action of β-alanyl and L-histidine through carnosine synthase. Research reports show that carnosine not only has the effect of delaying aging, but also has the beneficial effect of reversing the aging form of aged cells. Carnosine is (belongs to) an antioxidant and can capture oxygen free radicals. In the presence of pyruvate, L-carnosine can select It can kill tumor cells and transformed cells. L-carnosine also has the function of increasing serum insulin and reducing glucagon to achieve the effect of controlling blood sugar levels. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K1/02C07K1/06C07K1/14
CPCY02P20/55
Inventor 钱祥云王永兴陆建刚
Owner SUZHOU FUSHILAI PHARMA CO LTD
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