Method for enhancing production yield and rate of esomeprazole

A kind of technology of esomeprazole and product yield, applied in the field of drug synthesis

Active Publication Date: 2013-07-31
CP PHARMA QINGDAO CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

No one has tried to use the high-efficiency catalytic properties of the chira

Method used

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  • Method for enhancing production yield and rate of esomeprazole

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Effect test

Embodiment 1

[0020] Weigh 100g of sulfide with an electronic balance, dissolve it in 500ml of dichloromethane, stir at 25-30°C for 30min, add chiral catalyst 0.091molMn (salen), 0.213molD-(-)diethyl tartrate, and stir at 55°C for 25min. Lower the temperature to 15~25°C, add 50g of cumene hydroperoxide, and complete the oxidation in 20 minutes. Add n-hexane, filter out Mn (salen), then distill off dichloromethane and n-hexane, and finally add 600ml of acetone to dissolve esomeprazole at room temperature, and then raise the temperature to 53°C for crystallization. Obtain about 92g of esomeprazole fine product, and it is 99.8% to obtain esomeprazole content by high performance liquid phase detection.

Embodiment 2

[0022] Weigh 50g of sulfide with an electronic balance, dissolve it in 250ml of dichloromethane, stir at 25-30°C for 30min, add chiral catalyst 0.045molMn (salen), 0.106molD-(-)diethyl tartrate, and stir at 55°C for 25min. Lower the temperature to 15-25°C, add 25g of cumene hydroperoxide, and complete the oxidation in 20 minutes. Add n-hexane, filter out Mn (salen), then distill off dichloromethane and n-hexane, and finally add 300ml of acetone to dissolve esomeprazole at room temperature, and heat up to 53°C for crystallization after dissolution. Obtain about 45g of esomeprazole fine product, and it is 99.8% to obtain esomeprazole content by high performance liquid phase detection.

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Abstract

The invention aims to enhance the conversion and generation yield and rate of esomeprazole from omeprazole precursor-thioether through a chiral catalyst Mn(salen). The method comprises the following steps: weighing a right amount of esomeprazole precursor-thioether, evenly mixing with dichloromethane, adding the chiral catalyst Mn(salen) and D-(-)diethyl tartrate to carry out chiral conversion, adding cumene hydroperoxide for oxidation to generate esomeprazole, filtering to remove the chiral catalyst, distilling out dichloromethane to obtain an esomeprazole crude product, and finally, crystallizing with acetone to obtain the esomeprazole pure product. High-performance liquid chromatography is utilized to detect the content. The chiral catalyst Mn(salen) can enhance the generation yield of esomeprazole sodium by 50%, and save the reaction time by 2 hours or so. The method is simple to operate, and has the advantages of low reagent toxicity, low required initial raw material cost and high product yield.

Description

technical field [0001] The invention relates to a method for improving the production yield and rate of esomeprazole, through the high-efficiency catalysis of the chiral catalyst Mn (salen), the yield of esomeprazole is increased by 50%, and the reaction time is shortened by nearly 2 hours , greatly increasing the reaction rate. It belongs to the technical field of drug synthesis. Background technique [0002] Esomeprazole is the levorotatory form of omeprazole, the first optically pure proton pump inhibitor on the market, and is currently the best medicine for treating gastric acid without side effects. [0003] At present, the research on this type of drug has been relatively in-depth at home and abroad, and its synthetic route basically uses tetraisopropyl titanate as a catalyst to catalyze the oxidation of thioether to synthesize esomeprazole. At present, the synthetic method of the patent "Synthetic method of substituted thionoid compounds" (Patent No. 95194956.X) use...

Claims

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Application Information

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IPC IPC(8): C07D401/12
Inventor 王明刚任莉陈阳生牛建兴臧云龙汪泓
Owner CP PHARMA QINGDAO CO LTD
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