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A kind of synthetic method of ursodeoxycholic acid

A technology of ursodeoxycholic acid and synthesis method, which is applied in the field of ursodeoxycholic acid synthesis, can solve the problems of poor reaction selectivity and high cost, and achieve the effects of mild reaction conditions, low cost and environmental friendliness

Active Publication Date: 2020-12-22
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] (3) Use deoxycholic acid as raw material to synthesize ursodeoxycholic acid, as shown in the following route (III) (CN 103319560 A), this synthetic route uses chenodeoxycholic acid as raw material to synthesize ursodeoxycholic acid, although Yield (86%) is higher, but with chenodeoxycholic acid as raw material, the cost is higher, in addition to cerium trichloride and sodium borohydride reduction 7-carbonyl is the reaction selectivity of this step of 7β-hydroxyl is poor

Method used

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  • A kind of synthetic method of ursodeoxycholic acid
  • A kind of synthetic method of ursodeoxycholic acid
  • A kind of synthetic method of ursodeoxycholic acid

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Embodiment 1

[0091] 1. Preparation of the compound of formula (2): Dissolve cholic acid (9g, 22.0mmol) in 200mL acetone / water (v / v=3:1), keep away from light, slowly add NBS (5.7g, 31.9mmol), Reaction at room temperature 25°C for 2h. After the TLC detection reaction is complete, add 100mL saturated sodium bisulfite solution to quench the reaction, concentrate under reduced pressure until a white solid appears, and stop when poured into 1L of water to precipitate a large amount of white solid, which is left to crystallize, filtered and dried to obtain the formula (2) Compound (8.5 g white solid, yield 95%). used directly in the next step.

[0092]

[0093] 2. Preparation of the compound of formula (3-1): Dissolve the compound of formula (2) (8.5g, 20.9mmol) in 100mL of methanol, add 1mL of concentrated sulfuric acid, heat to reflux for 2h, concentrate under reduced pressure to remove methanol, add 30mL of water, The aqueous phase was extracted with dichloromethane (30 mL x 3). Combine...

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Abstract

The invention discloses a synthesis method of ursodesoxycholic acid. The ursodesoxycholic acid is synthesized by using cholic acid as a raw material through the steps of 7alpha-hydroxyl selective oxidation, side chain carboxyl esterification, 3alpha-hydroxyl esterification, 12alpha-hydroxyl methanesulfonic acid esterification, elimination, hydrolysis, reduction and the like. The synthesis method of the ursodesoxycholic acid is simple in the steps, few in side reactions, high in yield, accessible in the raw material and applicable to industrial production, and solves the problems of high synthesis cost, low yield and the like in the prior art, thereby having wide application prospects.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, in particular to a method for synthesizing ursodeoxycholic acid. Background technique [0002] Ursodeoxycholic acid can promote the secretion of endogenous bile acids and reduce reabsorption; antagonize the cytotoxicity of hydrophobic bile acids and protect liver cell membranes; dissolve cholesterol gallstones and have immunoregulatory effects. Commonly used drugs. In 2015, my country's ursodeoxycholic acid market was about 850 million, but 95% of the hospital market was imported products, and Germany's Falk Pharmaceuticals had the largest market share. Sales in China reached 660 million RMB. [0003] Studying the chemical preparation method of ursodeoxycholic acid and improving the production technology level are the biggest technical difficulties faced by domestic enterprises. Therefore, it is of great social significance and economic value to develop a green, economical, efficient and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J9/00
CPCC07J9/005
Inventor 仇文卫
Owner EAST CHINA NORMAL UNIV