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New synthetic method of Caronic anhydride

A synthetic method, the technology of chrysanthemic acid ester, which is applied in the new field of synthesizing carronic acid anhydride, can solve the problems of uneconomical, unenvironmental protection, unsuitable for large-scale industrial production, etc., and achieve the effect of high yield and low cost

Inactive Publication Date: 2012-03-28
JIANGSU YANGNONG CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses a large amount of potassium permanganate and concentrated sulfuric acid as raw materials, resulting in manganese-containing residue and waste acid, which is neither economical nor environmentally friendly, and is not suitable for large-scale industrial production.

Method used

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  • New synthetic method of Caronic anhydride
  • New synthetic method of Caronic anhydride
  • New synthetic method of Caronic anhydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Step 1: in 500mL flask, add 200g ethyl acetate, drop into permethrin ethyl 94.8g (0.4mol) again, cool down to-5 ℃, begin to pass into the ozone of volume concentration 3% with the flow rate of 2L / min ( The remainder is air, the same below) to react, during the reaction process, carry out central control analysis of raw materials by gas spectrometry, and stop passing ozone after the conversion rate of ethyl permethrin is greater than 99%. After the reaction, add water, wash and separate the oil layer with water, wash twice, each time with 100ml of water, and after the washing is completed, the oil layer is concentrated by rotary evaporation to remove the solvent, and then 70g of 30% liquid caustic soda is added dropwise to the remaining reaction-finished material to carry out Saponification reaction, at this time, the pH is greater than 12, and the temperature is kept at 50-60°C for 2 hours, and then 30% hydrochloric acid is added dropwise to the reaction liquid for acidi...

Embodiment 2

[0031] Step 1: Add 80g of 50% mass concentration of acetic acid aqueous solution into a 500mL flask, then add 80g (0.4mol) of DE chrysanthemum acid ethyl ester, cool down to 10°C, and start to feed ozone with a volume concentration of 1.5% at a flow rate of 3L / min Carry out the reaction, and carry out central control analysis through gas spectrum during the reaction process, and stop passing ozone after the conversion rate of ethyl chrysanthemum acid is greater than 99%. After the reaction is completed, the layers are separated, and then 90g of 30% liquid caustic soda is added dropwise to the above-mentioned reaction finished material to carry out saponification reaction. % hydrochloric acid acidification reaction until the pH value reaches 1-2, the reaction temperature is controlled at 40-50°C, and the reaction is kept for 1 hr. After cooling down to room temperature, extract with methyl tert-butyl ether, 100ml each time, extract three times in total, combine the obtained org...

Embodiment 3

[0034] Step 1: Add 300g of acetone to a 500mL flask, then add 89.2g (0.4mol) of permethrin methyl ester, cool down to -20°C, and start to feed ozone with a volume concentration of 8% at a flow rate of 0.5L / min for reaction ,, during the reaction process, the gas spectrum is used to analyze the raw materials in the central control, and after the conversion rate of methyl permethrin is greater than 99%, the ozone is stopped. After the reaction, add water, wash and separate the oil layer with water, and concentrate the oil layer to remove the solvent, then add 70g of 30% liquid caustic soda dropwise to the above reaction-finished material to carry out saponification reaction. At this time, the pH is greater than 12. Insulate and react at ℃ for 2 hours, then add 30% hydrochloric acid dropwise to the reaction solution to acidify the reaction until the pH value reaches 1-2, control the reaction temperature at 40-50 ℃, and insulate for 1 hr. After cooling down to room temperature, ex...

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Abstract

The invention provides a new synthetic method of 6,6-dimethyl-3-oxiabicyclo[3.1.0]hexane-2,4-dione (Caronic anhydride). According to the method, chrysanthemum monocarboxylate which has a structure represented by formula (I) is oxidized with a clean ozonization technology, and the obtained oxidation product is saponified and acidified to generate 3,3-dimethyl-1,2-cyclopropanedicarboxylic acid, R1 in the formula (I) is methyl or chlorine, and R2 in the formula (I) is methyl or ethyl; and 3,3-dimethyl-1,2-cyclopropanedicarboxylic acid is subjected to a dehydration ring-closure reaction in a system of acetic anhydride and sodium acetate to generate the Caronic anhydride. Compared with the prior art, the new method of the invention, which allows no waste acids to be generated, is a green production technology.

Description

technical field [0001] The invention relates to a synthesis method of a pharmaceutical intermediate 6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione (caronic anhydride). Background technique [0002] Caronic anhydride (Caronic anhydride) is a pharmaceutical intermediate, mainly used for the synthesis of oral hepatitis C protease inhibitor Boceprevir (SCH 503034). Boceprevir is an oral hepatitis C protease inhibitor developed by Schering-Plough. The first indication that Boceprevir is suggested is for the treatment of HCV (hepatitis C virus) genotype 1 virus-infected patients who do not respond to the standard treatment—pegylated interferon and ribavirin combination therapy. Boceprevir is a new type of HCV inhibitor, an orally active inhibitor of hepatitis C virus serine protease, which can inhibit the replication of HCV, and is also used to treat chronic hepatitis C infection. [0003] The structures of caronic anhydride and Boceprevir are as follows: [0004] [0005]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/93
Inventor 戚明珠朱建荣贺书泽姜友法戈素兵赵鹏谢邦伟
Owner JIANGSU YANGNONG CHEM
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