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Preparation method of medicine intermediate butanone diacid diester compound

A technology of isobutanedate diesters and compounds, which is applied in the field of preparation of pharmaceutical intermediates butanedate diesters, can solve the problems of unsuitability for industrial production, harsh reaction conditions, and low yield, and achieve catalyst Cheap and easy to obtain, mild reaction conditions and high yield

Inactive Publication Date: 2012-06-20
SHANGHAI HUAYI GRP CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods can only be aimed at the condensation reaction of diethyl oxalate and ethyl acetate, and these processes have the disadvantages of harsh reaction conditions, high toxicity, high cost, low yield, etc., and are not suitable for industrial production

Method used

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  • Preparation method of medicine intermediate butanone diacid diester compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a reactor equipped with freezing, stirring, and a thermometer, 150ml of furan, 11.8g (0.1mol) of dimethyl oxalate, and 5.4g (0.1mol) of sodium methoxide were respectively added. Dissolve 8.2g (0.11mol) of methyl acetate in 50ml of furan, control the temperature in an ice-water bath at 5°C, add the methyl acetate / furan mixture dropwise to the dimethyl oxalate / furan mixture with stirring, within 2 hours After the dropwise addition, react at 5°C for another 2h, remove the ice-water bath, install a reflux condenser in the reactor, slowly raise the temperature to 30°C, and react for 6h. Wash with dilute hydrochloric acid to acidify the reaction solution to weak acidity, separate the liquids, wash twice with saturated sodium chloride solution, separate the liquids, dry over anhydrous sodium sulfate, filter, and recover furan by distillation under reduced pressure to obtain 8.7 g of butanone diacid Dimethyl ester, yield 52.2%, content (GC) 95.9%.

Embodiment 2

[0024] In a reactor equipped with freezing, stirring, and a thermometer, 150 ml of tetrahydrofuran, 11.8 g (0.1 mol) of dimethyl oxalate, and 2.7 g (0.05 mol) of sodium methoxide were respectively added. Dissolve 7.4g (0.1mol) of methyl acetate in 50ml of tetrahydrofuran, control the temperature in an ice-water bath at 5°C, and add the methyl acetate / tetrahydrofuran mixture dropwise to the dimethyl oxalate / tetrahydrofuran mixture with stirring, within 2 hours After the dropwise addition, react at 5°C for another 4h, remove the ice-water bath, install a reflux condenser in the reactor, slowly raise the temperature to 40°C, and react for 4h. Wash with dilute hydrochloric acid to acidify the reaction solution to weak acidity, separate the liquids, wash twice with saturated sodium chloride solution, separate the liquids, dry over anhydrous sodium sulfate, filter, and distill under reduced pressure to recover tetrahydrofuran to obtain 14.4 g of butanone diacid Dimethyl ester, yield...

Embodiment 3

[0026] In a reactor equipped with refrigeration, stirring, and a thermometer, 150ml of 2-methyltetrahydrofuran, 11.8g (0.1mol) of dimethyl oxalate, and 5.4g (0.1mol) of sodium methoxide were respectively added. Dissolve 11.1g (0.15mol) of methyl acetate in 100ml of 2-methyltetrahydrofuran, control the temperature in an ice-water bath at 0°C, and add the mixture of methyl acetate / 2-methyltetrahydrofuran dropwise to dimethyl oxalate under stirring / 2-Methyltetrahydrofuran mixture, the dropwise addition was completed within 2 hours, reacted at 0°C for another 2h, removed the ice-water bath, installed a reflux condenser for the reactor, slowly raised the temperature to 60°C, and reacted for 2h. Wash with dilute hydrochloric acid to acidify the reaction solution to weak acidity, separate the liquids, wash twice with saturated sodium chloride solution, separate the liquids, dry over anhydrous sodium sulfate, filter, and recover 2-methyltetrahydrofuran by distillation under reduced pr...

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Abstract

The invention discloses a preparation method of a medicine intermediate butanone diacid diester compound. The butanone diacid diester compound is obtained by treating a furan compound as a solvent, an oxalic acid diester compound and an acetate compound as raw materials, and an organic alkali as a catalyst, reacting for 1-6h under low temperature conditions, heat-reacting for 1-8h, and processing. Detection results show that the purity of the butanone diacid diester compound is equal to or greater than 95%, and the yield of the butanone diacid diester compound is 50-90%. The preparation method of the invention, which has the advantages of mild reaction mild, small toxicity and easy recycle of the solvent, cheap and easily available catalyst, simple post-processing, less waste gas, waste water and water residue, and high yield, is suitable for the industrialization production.

Description

technical field [0001] The present invention relates to the preparation method of the butanone diacid diester compound which is a pharmaceutical intermediate, in particular to a method for synthesizing butanone under the catalysis of an organic base by using a furan compound as a solvent, an oxalic acid diester compound and an acetate compound as raw materials A new approach to diacid diesters. Background technique [0002] Butanone dioic acid diesters are mainly used as intermediates in drug synthesis, and their most important use is as the most basic raw material for the synthesis of orotic acid (vitamin B13), which is widely used in the fields of medicine, food, daily chemicals, and life sciences . [0003] In the field of medicine, orotic acid and its derivatives are widely used. It is a good liver-protecting drug in itself, and has good curative effects on jaundice liver disease, fatty liver, and acute and chronic hepatitis. At present, a series of drugs based on orot...

Claims

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Application Information

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IPC IPC(8): C07C69/716C07C67/343
Inventor 张传好代立顾慧娟廖本仁
Owner SHANGHAI HUAYI GRP CO
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