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2-hexyl-3-hydroxy-5-r1-oxy hexadecyl carboxylic r2 ester and its prepn and use in preparing orlistat as slimming medicine

A technology of oxyhexadecanoic acid, -5-R1, applied in the field of preparing orlistat, can solve the problems of high production cost, low yield and production efficiency, etc.

Inactive Publication Date: 2007-11-07
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield and production efficiency of this method are not high, resulting in higher production costs of orlistat

Method used

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  • 2-hexyl-3-hydroxy-5-r1-oxy hexadecyl carboxylic r2 ester and its prepn and use in preparing orlistat as slimming medicine
  • 2-hexyl-3-hydroxy-5-r1-oxy hexadecyl carboxylic r2 ester and its prepn and use in preparing orlistat as slimming medicine
  • 2-hexyl-3-hydroxy-5-r1-oxy hexadecyl carboxylic r2 ester and its prepn and use in preparing orlistat as slimming medicine

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Embodiment Construction

[0072] (The following examples will help to understand the present invention, but do not limit the content of the present invention.)

[0073] first step

[0074]

[0075]Take a 100ml three-neck bottle, and after baking and ventilating, it can achieve anhydrous and oxygen-free operation. Magnesium chips (2.5 g, 0.104 mol), 18 ml of anhydrous tetrahydrofuran, and catalytic amount (0.05 ml) of 1,2-dibromoethane were sequentially added thereto. Put the above reaction in a water bath, add a solution of decane bromide (20.8ml, 98mmol) in 20ml of anhydrous toluene dropwise, and keep the temperature at about 40°C. After the dropwise addition, stir at room temperature for 0.5 h, then raise the temperature and reflux for 0.5 h, and the reaction solution is clear at this time. In the formula, dry THF / Toluene represents anhydrous tetrahydrofuran / toluene solvent.

[0076] Another 100ml three-neck bottle was taken, and it was operated anhydrous and oxygen-free. Add cuprous iodide (1...

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Abstract

The present invention is compound (2S, 3S, 5S)-2-hexyl-3-hydroxy-5-R1-oxy hexadecyl carboxylic acid R2 ester and its synthesis process and application in preparing orlistat as slimming medicine. The present invention prepares the ultimate product orlistat with (S)-chloroepoxy propane as initial material and through the first five reaction steps to obtain optically active intermediate, and the subsequent stereo selective reduction, alpha position alkylation, condensation with side chain amino acid and other reactions. The process is simple, easy to operate and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, relates to a new synthetic method, more specifically relates to the preparation chemical name: (S)-2-formamido-4-methyl-pentanoic acid (S)-1-[[(2S , 3S)-3-hexyl-4-oxo-2-oxetane] methyl]-dodecyl ester of a new synthetic method of weight loss drug orlistat; the present invention relates to a method of orlistat A new type of intermediate, its preparation method and its use for the preparation of orlistat. Background technique [0002] Orlistat is a lipase inhibitor. With the participation of bile salts, it forms an inactive intermediate with gastrointestinal lipase, which irreversibly inhibits the enzyme, thereby weakening the digestion and absorption of fat, keeping the intestinal tract in an oil phase state, and sequestering cholesterol and passing it through Fecal excretion. Orlistat (Orlistat) was approved by the U.S. FDA on April 23, 1999 for the treatment of obesity, with a trade name of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/675C07C229/06C07D305/12
CPCY02P20/55
Inventor 马大为吴清泉徐鹏
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI