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Synthetic method for N-acetyl carnosine

A synthesis method and acetyl carnosine technology, which are applied in the field of N-acetyl carnosine synthesis, can solve the problems of difficult extraction and separation, high price, and difficulty in extraction, separation and purification, and achieve the effects of reasonable process and simple operation.

Active Publication Date: 2015-12-16
江西海思加生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has many disadvantages: First, although carnosine has been produced industrially, it is still relatively expensive compared to starting materials such as histidine and β-alanine. Second, acetylation is difficult to guarantee due to the relatively high activity of acetyl groups. Partial acetylation on the histidine side chain
Third, since the solubility of the product and raw materials in organic solvents is not good, and the solubility in water is very good, it is difficult to extract, separate and purify
Another method directly uses Ac-β-alanine and histidine to synthesize, but the Ac-β-alanine method is difficult to extract and separate through organic solvents, and it is difficult to carry out in the production process

Method used

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  • Synthetic method for N-acetyl carnosine
  • Synthetic method for N-acetyl carnosine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Synthesis of N-2,4,6-trimethoxybenzyl-β-alanine methyl ester

[0025] Dissolve 10.4 grams of 2,4,6-trimethoxybenzaldehyde in 300 milliliters of dichloromethane, add 11 milliliters of triethylamine, 11.2 grams of β-alanine methyl ester hydrochloride, and 22 grams of sodium acetate borohydride, React at room temperature for 24 hours, add saturated aqueous sodium bicarbonate to separate layers, extract with dichloromethane, wash with water, dry over anhydrous sodium sulfate, filter, and concentrate to obtain N-2,4,6-trimethoxybenzyl-β-alanine methyl Ester oil. The product was directly used in the next reaction without treatment.

[0026] (2) Synthesis of N-acetyl N-2,4,6-trimethoxybenzyl-β-alanine methyl ester

example 1

[0027] The product in Example 1 was dissolved in 100ML of dichloromethane, 14 milliliters of triethylamine was added under stirring, under ice-water bath, 12 milliliters of acetic anhydride was added dropwise, and the temperature was controlled below 10 degrees. Add water, adjust the pH to 1-2 with hydrochloric acid, separate the layers, extract with dichloromethane, wash with saturated brine, dry over anhydrous sodium sulfate, and decolorize. Spin-dry to obtain 17 grams of oil.

[0028] (3) Synthesis of N-acetyl N-2,4,6-trimethoxybenzyl-β-alanine

[0029] Dissolve 8.9 g of N-acetyl N-2,4,6-trimethoxybenzyl-β-alanine methyl ester in 50 ml of methanol, add 20 ml of 4N sodium hydroxide aqueous solution, react for 2 hours, and then adjust the pH with 6N HCl After stirring at 4, a solid precipitated out to obtain a solid, which was washed with ether and dried to obtain 7 g of a solid.

[0030] (4) Synthesis of N-acetyl N-2,4,6-trimethoxybenzyl-β-alanyl-L-histidine

[0031] Add ...

Embodiment 2

[0037] A kind of synthetic method of N-acetylcarnosine, this method comprises the following steps:

[0038](1) Synthesis of N-2,4,6-trimethoxybenzyl-β-alanine methyl ester: using β-alanine methyl ester as starting material, 2,4,6-trimethoxybenzene Formaldehyde and β-alanine methyl ester are reduced by sodium acetate borohydride to obtain N-2,4,6-trimethoxybenzyl-β-alanine methyl ester; the 2,4,6-trimethoxy The mass ratio of benzaldehyde, β-alanine methyl ester, and sodium acetate borohydride is in the range of 1:1:2;

[0039] The 2,4,6-trimethoxybenzaldehyde is dissolved in an organic solvent, and then reacted with β-alanine methyl ester and sodium acetate borohydride. The reaction temperature is room temperature, and the reaction time is 24 hours. The organic solvent is a mixture of dichloromethane and triethylamine in a volume ratio of 300:11.

[0040] (2) Synthesis of N-acetyl N-2,4,6-trimethoxybenzyl-β-alanine methyl ester: N-2,4,6-trimethoxybenzyl-β-alanine obtained in ...

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Abstract

The invention relates to a synthetic method for N-acetyl carnosine comprising using [beta]-alanine methyl ester as an initial raw material, raising the dissolvability of [beta]-alanine methyl ester in an organic solvent and reducing the dissolvability in water, by modifying the amino group into 2,4,6-trimethoxy benzal group, hydrolyzing to remove methyl ester after acetylating the amino group, carrying out a condensation reaction with histidine methyl ester, protecting by a strong acid after hydrolyzing to remove methyl ester, absorbing by a strong acid cation resin, eluting by ammonia water to obtain N-acetyl carnosine. Compared with the prior art, the synthetic method for N-acetyl carnosine can effectively overcome the problems of difficulty of separating intermediates and usage of expensive raw material carnosine, and another synthetic method for N-acetyl carnosine is provided.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a synthesis method of N-acetylcarnosine. Background technique [0002] Senile cataract is a phenomenon in which the lens of the eye becomes cloudy due to oxidation, causing poor vision or even blindness. As a natural oxidation inhibitor, N-acetyl-carnosine can inhibit the oxidation of the lens of the eyeball. N-acetyl-L-carnosine eye drops can treat senile cataract diseases, and the market potential is huge. In addition, N-acetyl-L-carnosine also has a good cosmetic effect, and has the ideal effect of anti-wrinkle, anti-aging and repairing skin damage. Because carnosine is industrialized production, so many synthetic methods all start to synthesize from carnosine, as CN101077863A (the improved method of chemically synthesizing N_acetyl_L_ carnosine), Japanese Patent JP58124750A or the like. This method has many disadvantages: First, although ca...

Claims

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Application Information

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IPC IPC(8): C07D233/64
Inventor 严承飞俞建新金萍顾建良
Owner 江西海思加生物科技有限公司
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