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Weight-reducing medicine orlistat synthesis method

A technology of orlistat and a synthesis method, applied in the field of drug synthesis, can solve the problems of long hydrogenation reaction time, low yield and the like, and achieve the effects of easy product purification, few side reactions and fast reaction speed

Inactive Publication Date: 2017-05-10
QINGDAO CHENDA BIOLOGICAL SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to overcome the defects of long hydrogenation reaction time and low yield in the existing process of preparing orlistat, and provide a synthetic method of orlistat with short reaction time, simple steps and high yield

Method used

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  • Weight-reducing medicine orlistat synthesis method

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Effect test

Embodiment 1

[0019] Synthesis of orlistat

[0020] Under nitrogen protection, 9.8g of niborestatin, (R,R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexyldi Add 0.7g of cobaltamine, 0.6g of cuprous chloride and 30ml of acetonitrile into the reaction flask, start stirring, adjust the temperature to 20°C, then add 2.3g of sodium borohydride in three batches and stir for 2 to 4 hours. After the reaction is complete, the The reaction solution was poured into ice water to quench the reaction, extracted with dichloromethane, washed with water, and the organic phase was concentrated under reduced pressure to obtain orlistat. Dissolve the obtained orlistat in dichloromethane / petroleum ether mixed solvent (volume ratio 1:20), then heat to 80°C and stir for 10-20 minutes, filter while hot, cool the filtrate naturally, suction filter, and vacuum-dry to obtain refined 9.3 g of orlistat, the yield was 94.3%, and the HPLC purity was 99.56%.

Embodiment 2

[0022] Synthesis of orlistat

[0023] Under nitrogen protection, 9.8g of niborestatin, (R,R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexyldi Add 0.6g of cobaltamine, 0.6g of cuprous chloride and 30ml of acetonitrile into the reaction flask, start stirring, adjust the temperature to 15°C, then add 3g of sodium borohydride in three batches and stir for 2 to 4 hours. After the reaction is complete, the reaction The solution was poured into ice water to quench the reaction, extracted with dichloromethane, washed with water, and the organic phase was concentrated under reduced pressure to obtain orlistat. The obtained orlistat was dissolved in dichloromethane / petroleum ether mixed solvent (volume ratio 1:20), then heated to 70°C and stirred for 10-20 minutes, filtered while hot, the filtrate was naturally cooled, suction filtered, and vacuum-dried to obtain refined 9.4 g of orlistat, the yield was 95.2%, and the HPLC purity was 99.66%.

Embodiment 3

[0025] Synthesis of orlistat

[0026] Under nitrogen protection, 9.8g of niborestatin, (R,R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexyldi Add 0.9g of cobaltamine, 0.4g of cuprous chloride and 30ml of acetonitrile into the reaction flask, start stirring, adjust the temperature to 10°C, then add 3.8g of sodium borohydride in three batches and stir for 2 to 4 hours. After the reaction is complete, the The reaction solution was poured into ice water to quench the reaction, extracted with dichloromethane, washed with water, and the organic phase was concentrated under reduced pressure to obtain orlistat. Dissolve the obtained orlistat in dichloromethane / petroleum ether mixed solvent (volume ratio 1:20), then heat to 80°C and stir for 10-20 minutes, filter while hot, cool the filtrate naturally, suction filter, and vacuum-dry to obtain refined 9.4 g of orlistat, the yield was 94.5%, and the HPLC purity was 99.76%.

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Abstract

The invention discloses a weight-reducing medicine orlistat synthesis method. The synthesis method includes that in existence of (R,R)-(-)-N,N'-bis(3,5-ditert-butyl-salicylidene)-1,2-cyclohexyl diamine cobalt, lipstatin and sodium borohydride are subjected to reduction reaction under catalysis of cuprous chloride to obtain orlistat. The orlistat synthesis method is quick in reaction, and reaction yield is increased effectively. By adoption of (R,R)-(-)-N,N'-bis(3,5-ditert-butyl-salicylidene)-1,2-cyclohexyl diamine cobalt as a stabilizer of a reducing agent, low side reaction quantity, easiness in product purification and suitableness for industrial expanded production are realized.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a method for synthesizing weight loss drug orlistat. Background technique [0002] Orlistat (Orlistat), the chemical name is (S)-2-formamido-4-methyl-pentanoate (S)-1-[[(2S,3S)-3-hexyl-4-oxo -2-Oxetanyl]-methyl]-dodecyl ester. Orlistat is a new type of weight-loss drug developed by Roche. It forms a covalent bond through the active serine site of gastric lipase and pancreatic lipase in the stomach and small intestine, which inactivates the lipase activity and prevents the decomposition of fat in the fifteenth middle-aged drug. Absorption and utilization, so as to achieve the purpose of weight loss. Compared with other weight loss drugs, its advantage is that orlistat does not act on the nervous system, does not enter the blood, and does not suppress appetite. [0003] At present, the preparation of orlistat is mainly divided into two types, one is microbial fermentati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D305/12
CPCC07D305/12
Inventor 吕燕华
Owner QINGDAO CHENDA BIOLOGICAL SCI & TECH
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