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Method for synthesizing ursodesoxycholic acid with chenodeoxycholic acid by photochemical method

A technique for chenodeoxycholic acid and ursodeoxycholic acid is applied in the field of preparation of ursodeoxycholic acid, can solve problems such as poor stereoselectivity, and achieve the effects of stable quality, mild reaction conditions and high purity

Inactive Publication Date: 2016-03-23
四川新功生物科技集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of them use alcohol + metal sodium system for hydrogenation reduction reaction. This system has poor stereoselectivity during hydrogenation reduction reaction. Only about 80% of 7-ketolithocholic acid is reduced to ursodeoxycholic acid, and the other 20 % reduced to chenodeoxycholic acid, after the reaction is completed, it needs to be separated and purified, and the final ursodeoxycholic acid product is only about 60% of chenodeoxycholic acid

Method used

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  • Method for synthesizing ursodesoxycholic acid with chenodeoxycholic acid by photochemical method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A kind of photochemical method uses chenodeoxycholic acid to synthesize the method for ursodeoxycholic acid, it comprises the following steps:

[0037] A, Preparation of methyl chenodeoxycholate

[0038] Take 39.2g of chenodeoxycholic acid (99.4% content) and dissolve it in 200mL of methanol, stir at room temperature until it dissolves completely, then slowly add 5mL of 98% concentrated sulfuric acid, stir at room temperature for 4 hours, and confirm the reaction is complete by spotting samples by thin-layer chromatography After adding 7.92g of sodium hydroxide, stirring and neutralizing sulfuric acid, when the pH was 6 to 8, the neutralization product sodium sulfate was removed by filtration; the filtrate was concentrated to obtain 41g of methyl chenodeoxycholic acid, which was determined by high performance liquid chromatography. Oxycholic acid methyl ester content is 97.3%;

[0039] B, Preparation of 3α-hydroxy-7-keto-5β-cholanoic acid methyl ester by photochemical ...

Embodiment 2

[0045] A kind of photochemical method uses chenodeoxycholic acid to synthesize the method for ursodeoxycholic acid, it comprises the following steps:

[0046] A, Preparation of methyl chenodeoxycholate

[0047]Take 39.2 g of chenodeoxycholic acid (99%) and dissolve it in 200 mL of methanol, stir at room temperature until it is completely dissolved, then slowly add 5 mL of 98% concentrated sulfuric acid, stir at room temperature for 4 hours, and confirm that the reaction is complete by applying thin-layer chromatography. Add sodium hydroxide, stir to neutralize sulfuric acid, and when the pH is 6 to 8, filter and remove the neutralized product sodium sulfate; Concentrate the filtrate to obtain 41.2g of chenodeoxycholic acid methyl ester, and determine chenodeoxychole Acid methyl ester content is 97%;

[0048] B, Preparation of 3α-hydroxy-7-keto-5β-cholanoic acid methyl ester by photochemical oxidation

[0049] Dissolve 40.6g of methyl chenodeoxycholic acid in 200mL of n-butan...

Embodiment 3

[0054] A kind of photochemical method uses chenodeoxycholic acid to synthesize the method for ursodeoxycholic acid, it comprises the following steps:

[0055] A, Preparation of methyl chenodeoxycholate

[0056] Take 39.2 g of chenodeoxycholic acid (99.2%) and dissolve it in 200 mL of methanol, stir at room temperature until it dissolves completely, then slowly add 5 mL of 98% concentrated sulfuric acid, stir at room temperature for 4 hours, and confirm that the reaction is complete by applying thin-layer chromatography Add sodium hydroxide, stir to neutralize sulfuric acid, and when the pH is 6 to 8, remove the neutralized product sodium sulfate by filtration; Concentrate the filtrate to obtain 41.3g of chenodeoxycholic acid methyl ester, and determine chenodeoxychole Acid methyl ester content is 97.1%;

[0057] B, Preparation of 3α-hydroxy-7-keto-5β-cholanoic acid methyl ester by photochemical oxidation

[0058] Dissolve 40.6g of methyl chenodeoxycholic acid in 200mL of n-b...

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Abstract

The invention discloses a method for synthesizing ursodesoxycholic acid with chenodeoxycholic acid by a photochemical method. The method comprises the following steps: preparing chenodeoxycholic acid methyl ester, preparing 3alpha-hydroxyl-7-keto-5beta-methyl cholanate by a photochemical oxidation process, preparing ursodesoxycholic acid methyl ester by a photochemical reduction method, and preparing ursodesoxycholic acid. The method mainly uses the photochemical method for converting chenodeoxycholic acid to ursodesoxycholic acid, the method has the advantages of mild reaction condition, high reaction efficiency and high selectivity; and the prepared ursodesoxycholic acid has the advantages of high yield, high purity and stable quality.

Description

technical field [0001] The invention relates to a preparation method of ursodeoxycholic acid, in particular to a method for synthesizing ursodeoxycholic acid with chenodeoxycholic acid by photochemical method. Background technique [0002] Ursodeoxycholic acid (3α, 7β-dihydroxy-5β-cholic acid, referred to as UDCA) is the main component of traditional Chinese medicine bear bile, which was mainly used to treat gallstone diseases. In recent years, foreign countries have reported the application of UDCA in the treatment of various acute and chronic liver diseases. New research shows that UDCA not only has a good effect on the treatment of primary biliary cirrhosis, primary sclerosing cholangitis, and chronic active hepatitis, but also can be used to treat chronic hepatitis and rejection after liver transplantation. [0003] Ursodeoxycholic acid has the same molecular formula as chenodeoxycholic acid and bovine cholic acid, but their three-dimensional structures are different. I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCC07J9/005
Inventor 张秀芳高蓉
Owner 四川新功生物科技集团有限公司
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