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Improved synthesis method of bifendate

A technology of biphenyl diester and synthesis method is applied in the field of improved synthesis of biphenyl diester, can solve problems such as complicated post-processing, and achieve the effects of avoiding column chromatography purification and shortening reaction steps

Active Publication Date: 2022-02-25
CANGZHOU PURUI DONGFANG SCI & TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006]In this reaction system, there are many reaction steps involved, and the post-treatment is relatively cumbersome, so it is necessary to improve the existing synthesis process

Method used

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  • Improved synthesis method of bifendate
  • Improved synthesis method of bifendate
  • Improved synthesis method of bifendate

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Embodiment 1

[0028] first step:

[0029] Add sulfolane 250mL, methylene bromide (24.4g, 0.14mol), potassium carbonate (69.0g, 0.50mol), potassium iodide (3.2g) and tetrabutylammonium iodide (1.5g) into the there-necked flask, stir evenly, and heat up To 75-80 ° C to form a uniform mixed solution. Control the temperature at 70-80°C and add gallic acid (17.0g, 0.1mol) / sulfolane 55mL solution dropwise. After the addition is complete, stir and raise the temperature to 95-100°C for 6 hours. TLC detects that the reaction of the raw materials is complete.

[0030] The reaction solution was lowered to room temperature and filtered, the solid was again slurried with sulfolane (60 mL), the filtrate was adjusted to pH = 2-3 by adding 10% hydrochloric acid, then 2.4 L of heptane solvent was added and stirred, and the precipitated solid was filtered. The solid was dissolved in dichloromethane, and the dichloromethane layer was washed twice with 2% hydrochloric acid aqueous solution, and the organic la...

Embodiment 2

[0039] first step:

[0040] Add sulfolane 220mL, methylene bromide (24.4g, 0.14mol), sodium carbonate (53.0g, 0.50mol), potassium iodide (1.3g) and tetrabutylammonium iodide (3.5g) into the there-necked flask, stir well, and heat up To 75-80 ° C to form a uniform mixed solution. Control the temperature at 70-80°C and add gallic acid (17.0g, 0.1mol) / sulfolane 55mL solution dropwise. After the addition is complete, stir and raise the temperature to 95-100°C for 6 hours. TLC detects that the reaction of the raw materials is complete.

[0041] The reaction solution was lowered to room temperature and filtered, the solid was again slurried with sulfolane (60 mL), the filtrate was adjusted to pH = 2-3 by adding 10% hydrochloric acid, then 2.4 L of heptane solvent was added and stirred, and the precipitated solid was filtered. The solid was dissolved in dichloromethane, and the dichloromethane layer was washed twice with 2% hydrochloric acid aqueous solution, and the organic layers ...

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Abstract

The invention relates to an improved synthesis method of bifendate, and belongs to the technical field of medical intermediates. The method comprises the following steps: reacting gallic acid serving as a raw material with dihalide under an alkaline condition to generate a cyclized substance, then reacting with dimethyl sulfate, and etherifying hydroxyl while carboxylic acid is esterified; and finally, deprotonating by adopting a large-steric-hindrance alkali, and coupling in the presence of anhydrous ferric trichloride to obtain the bifendate. The method only comprises three steps of reaction, and in the last step of reaction, isomers generated by coupling are pulped by a methyl tert-butyl ether / ethanol system and then removed to obtain a high-purity product bifendate. The method can be completed through three-step reaction, five-step reaction in the traditional process is avoided, the reaction steps are shortened, and the synthesis process is suitable for industrial amplification.

Description

technical field [0001] The invention relates to an improved synthesis method of bifendate, which belongs to the technical field of pharmaceutical intermediates. Background technique [0002] Biphenyl diester (full name 4,4-dimethoxy-5,6,5',6'-bis(methylenedioxy)biphenyl-2,2'-dihydroxy acid dimethyl ester), white The crystalline solid is a commonly used drug for the treatment of elevated transaminases caused by viral hepatitis and drug-induced liver injury. It has the pharmacological effects of protecting liver cells and increasing the detoxification function of the liver, especially its enzyme-lowering effect, which has obvious effects, low toxicity and small side effects. [0003] At present, the synthesis process of bifendate mainly uses gallic acid as raw material, and obtains bifendate after five-step reaction. The detailed process is as follows: [0004] [0005] In the first step, using gallic acid as a raw material, the carboxylic acid is converted into an ester ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/68
CPCC07D317/68
Inventor 刘宗伦王栋召冷辰宇张世红孟庆斌
Owner CANGZHOU PURUI DONGFANG SCI & TECH
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