Novel method for synthesizing L-carnosine

A new method and technology of carnosine, applied in the new synthesis field of L-carnosine, can solve the problems of reducing product yield, influence of product purity, toxicity of L-carnosine, etc., achieving the effect of low toxicity and side effects and meeting the requirements of medical consumption

Inactive Publication Date: 2008-02-06
ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is a common shortcoming in the multiple methods of synthesizing carnosine at present: due to being restricted by the side reaction, this side reaction is to carry out under the participation of the imidazole ring of L-histidine, and L-histidine has at least Racemization will occur above 0.8%, which reduces the yield of the product; it is difficult to s

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  • Novel method for synthesizing L-carnosine
  • Novel method for synthesizing L-carnosine

Examples

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Embodiment 1

[0016] The preparation of embodiment 1 phthalyl β-alanine (4)

[0017] In 500ml there-necked flask, drop into 111g (0.75mol) phthalic anhydride, β-alanine (2) 67g (0.75mol), heat up, along with the temperature rise of reaction material, material melts slowly into liquid state, simultaneously Start stirring, and when the temperature in the kettle reaches 175° C., control the temperature and keep warm for 25 minutes. After the heat preservation is completed, the material is poured into a crystallization dish and cooled naturally to obtain 164 g of white waxy crystals, with a yield of 99.8%.

Embodiment 2

[0018] The preparation of embodiment 2 phthaloyl β-alanyl chloride (5)

[0019] Put 1200g of toluene and 151g (0.69mol) of phthalyl β-alanine (4) into a 2000ml three-necked flask, stir in a water bath to raise the temperature, control the temperature below 60°C, and add 88.0g (0.74mol) of thionyl chloride dropwise. ), kept at 60-65°C for about 3 hours (making the system transparent), after the insulation was completed, concentrated toluene under reduced pressure to dryness, then added fresh toluene to entrain thionyl chloride, and dried to obtain 162g. The yield was 99%, add 800g chloroform, dissolve white phthaloyl β-alanyl chloride (5) and prepare for the next reaction.

Embodiment 3

[0020] Embodiment 3 Preparation of phthaloyl β-alanyl-L-histidine hydrochloride (6)

[0021] Put 92g (0.59mol) of L-histidine and 256.4g (2.36mol) of trimethylchlorosilane into a 2000ml nitrogen-protected flask, stir, and feed nitrogen at the same time to make it react under anoxic and anhydrous state. At the same time, turn on the heating to make it warm up and reflux, keep warm under the reflux state, absorb the released hydrogen chloride with water, wait for the reaction solution to become a homogeneous transparent solution, then stop the reaction, and concentrate under reduced pressure to dryness (control the temperature of the water bath to be no more than 50°C ), then add 200g toluene for 2-3 times to carry out entrainment, so that the reaction solution does not contain trimethylchlorosilane raw material, after entrainment is complete, drop to normal temperature to obtain intermediate (8); add 260g chloroform, and cool to 0-5 ℃, dropwise add the chloroformyl chloride (5)...

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Abstract

The invention discloses a synthesis method for L-Carnosine. In the prior art, the imidazole ring of the L-Histidine can take part in the reaction and has side-reactions, which decreases the yields of the products and makes the L-Carnosine assume the toxicity at the same time. In this invention, the o-phthalic anhydride is reacted with beta-alanine to produce the o-phthalic beta-alanine, the o-phthalic beta-alanine is made an acyl chlorination by the chloro-substitution reagent to synthesize into the o-phthalic beta-alanyl chloride; L-Carnosine is reacted with the edittrialkyl chlorosilane or hexamethyldisilazane to produce the trialky silane protection compound which is condensed with the o-phthalic beta-alanyl chloride to produce the hydrochloride; the hydrochloride is made a de-protection by the absolute alcohol, and then is neutralized by the basic solution to produce a product of neutralization; the hydrazine hydrate is used for a hydrazinolysis to the product of neutralization, then the L-Carnosine is precipitated from the absolute alcohol. The invention protects the imidazole ring on the L-Carnosine, avoids that the imidazole ring on the L-Carnosine makes side-reactions with other substances so as to obtain the pure L-Histidine, has low side-effects and high total yields as well as contents.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a new synthesis method of L-carnosine. Background technique [0002] Carnosine is a small molecule of natural dipeptide left-handed structure ubiquitous in nature. It is a dipeptide composed of β-alanine and L-histidine. Carnosine has cell anti-oxidation, anti-aging properties and a variety of physiological health care functions and medical effects. It has therapeutic effects on hypertension, heart disease, senile cataract, ulcer healing, etc. Exciting factors and other effects. There is a common shortcoming in the multiple methods of synthesizing carnosine at present: due to being restricted by the side reaction, this side reaction is to carry out under the participation of the imidazole ring of L-histidine, and L-histidine has at least Racemization will occur above 0.8%, which reduces the yield of the product; it is difficult to separate the L-carnosine with good optical puri...

Claims

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Application Information

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IPC IPC(8): C07D233/64C07K5/02
Inventor 陈建辉石明孝
Owner ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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