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Synthesis method of gastrodin

A synthesis method and technology of gastrodin, applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., to achieve the effects of low cost, stable quality, safe and easy operation

Active Publication Date: 2017-06-30
重庆西南制药二厂有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In view of the above deficiencies in the prior art, the object of the present invention is to provide a method for synthesizing gastrodin, which aims to solve the problem of potential safety hazards in the synthesis process of existing gastrodin

Method used

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  • Synthesis method of gastrodin
  • Synthesis method of gastrodin
  • Synthesis method of gastrodin

Examples

Experimental program
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Effect test

Embodiment 1

[0047] Add 300g of ethyl acetate to the reactor, then add 50g of potassium triacetoxyborohydride, then add 100g of 4-formylphenyl-2,3,4,6-tetra-0-acetyl-β-D-pyran Glucoside, the temperature is controlled at 20 to 30°C and the reaction is kept warm. Sampling is used to monitor the reaction by TLC. After 1 hour of reaction, the reaction is complete. The reaction solution is added to 300ml of water to quench, and then the upper organic phase is separated, and the organic phase is concentrated to a solid under vacuum. , then add 300g methanol and 22g diethylamine for reflux reaction for 2 hours, take a sample to monitor the reaction with TLC, add 10g activated carbon to decolorize for 10 minutes after the reaction is complete, filter, concentrate the filtrate to 1 / 3 of the original volume, and then add to the reaction solution Add 300g of acetone, stir and crystallize for 1 hour, filter to obtain 70g of gastrodin warm product, and dry at 70°C to obtain 55g of gastrodin dry product....

Embodiment 2

[0049] Add 300g of ethyl acetate to the reactor, then add 50g of sodium triacetoxyborohydride, then add 100g of 4-formylphenyl-2,3,4,6-tetra-0-acetyl-β-D-pyran The temperature of glucoside is controlled at 20 to 30°C for heat preservation reaction, and the reaction is monitored by TLC for sampling. After 2 hours of reaction, the reaction is complete. The reaction solution is added to 300ml of water to quench, and then the upper organic phase is separated, and the organic phase is concentrated to a solid under vacuum. Then add 300g methanol and 22g diethylamine for reflux reaction for 2 hours, take a sample to monitor the reaction with TLC, add 10g activated carbon to decolorize for 10 minutes after the reaction is complete, filter, concentrate the filtrate to 1 / 3 of the original volume, and then pour it into the reaction solution Add 300g of acetone, stir and crystallize for 1 hour, filter to obtain 65g of gastrodin warm product, and dry at 70°C to obtain 52g of gastrodin dry p...

Embodiment 3

[0051] Add 200g of ethyl acetate to the reactor, then add 50g of potassium triacetoxyborohydride, then add 100g of 4-formylphenyl-2,3,4,6-tetra-0-acetyl-β-D-pyran The temperature of glucoside is controlled at 20 to 30°C for heat preservation reaction, and the reaction is monitored by TLC for sampling. After 1.5 hours of reaction, the reaction is complete. The reaction solution is added to 300ml of water to quench, and then the upper organic phase is separated, and the organic phase is concentrated to a solid under vacuum. Then add 300g methanol and 22g diethylamine for reflux reaction for 2 hours, take a sample to monitor the reaction with TLC, add 10g activated carbon to decolorize for 10 minutes after the reaction is complete, filter, concentrate the filtrate to 1 / 3 of the original volume, and then pour it into the reaction solution Add 300g of acetone, stir and crystallize for 1 hour, filter to obtain 68g of gastrodin warm product, and dry at 70°C to obtain 53g of gastrodin ...

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Abstract

The invention discloses a synthesis method of gastrodin. The synthesis method of the gastrodin comprises the following steps: putting 4-formylphenyl-2,3,4,6-tetra-0-acetyl-beta-D-glucopyranoside and a reducing agent into a solvent, and conducting reaction at 0 to 30 DEG C for 0 to 3 hours; after complete reaction, adding water and performing quenching reaction; separating and taking an organic phase, concentrating the organic phase under the vacuum condition, and adding methanol in amount which is 2 to 5 times that of the organic phase; adding organic amine, performing refluxing reaction and performing alcoholysis; after complete reaction, adding activated carbon to decolor, filtering, concentrating, crystallizing and drying. By adoption of the synthesis method provided by the invention, the processes of the production process are reduced, and the method is safe, simple and convenient in operation, low in cost, low in pollution and suitable for large-scale production; furthermore, the prepared gastrodin product has stable quality and the purity is 99.9 percent or higher.

Description

technical field [0001] The invention relates to the field of drug synthesis, and mainly relates to a method for synthesizing gastrodin. Background technique [0002] The preparation of gastrodin by chemical synthesis is now mostly used by 4-formylphenyl-2,3,4,6-tetra-0-acetyl-β-D-glucopyranoside as an important intermediate through reduction, acetylation, produced by deprotection. At present, there are three main preparation methods: [0003] Method 1: 4-formylphenyl-2,3,4,6-tetra-0-acetyl-β-D-glucopyranoside is refluxed with potassium borohydride or sodium borohydride in an alcoholic solvent and then treated with vinegar Anhydride is acetylated, and then deprotected with sodium methoxide in an alcoholic solution, decolorized and recrystallized to obtain the finished product of gastrodin, and the synthetic route is shown in the following formula: [0004] [0005] The above method uses potassium borohydride or sodium borohydride to reduce under high-temperature reflux,...

Claims

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Application Information

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IPC IPC(8): C07H15/203C07H1/00
CPCC07H1/00C07H15/203
Inventor 王兴明
Owner 重庆西南制药二厂有限责任公司
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