Method for preparing ursodesoxycholic acid by chiral catalytic hydrogenation of 7-ketodesoxycholic acid

A technology of ketodeoxycholic acid and ursodeoxycholic acid, which is applied in the field of chiral catalytic hydrogenation of 7-ketodeoxycholic acid to generate ursodeoxycholic acid, can solve problems such as poor stereoselectivity, and achieves easy operation control, The effect of high yield and mild reaction conditions

Inactive Publication Date: 2011-05-25
ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 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-ketodeoxycholic acid is reduced to ursodeoxycholic acid. 20% is reduced to chenodeoxycholic acid. After the reaction is completed, it needs to be separated and purified. The final ursodeoxycholic acid product is only about 60% of chenodeoxycholic acid.

Method used

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  • Method for preparing ursodesoxycholic acid by chiral catalytic hydrogenation of 7-ketodesoxycholic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Replace the air in the hydrogenation reactor with nitrogen, add 100L of methanol, stir and dissolve, add 10Kg of 7-ketodeoxycholic acid, 4Kg of potassium ethoxide, and 0.2 grams of 1# catalyst. After replacing the nitrogen in the reactor with hydrogen, keep the hydrogen pressure in the reactor at 15Mpa, and react at room temperature for 5 hours. Distill to remove the solvent in the reaction kettle, add 200L purified water, stir to dissolve, adjust PH4 with 1:1 hydrochloric acid, centrifuge, wash the filter cake with purified water until the pH of the washing water is greater than 5. Vacuum dry at 75°C until the water content is less than 0.5%, and obtain Xiongqu Oxycholic acid 9.5Kg.

Embodiment 2

[0034] Replace the air in the hydrogenation reactor with nitrogen, add 100L of ethanol, stir and dissolve, then add 10Kg of 7-ketodeoxycholic acid, 4Kg of sodium bicarbonate, and 0.5g of 2# catalyst. After replacing the nitrogen in the reactor with hydrogen, keep the hydrogen pressure in the reactor at 10Mpa, and react at room temperature for 3 hours. Distill to remove the solvent in the reaction kettle, add 150L purified water, stir to dissolve, adjust PH3 with 1:2 sulfuric acid, centrifuge, wash the filter cake with purified water until the pH of the washing water is greater than 5. Vacuum dry at 75°C until the water content is less than 0.5%, and get Xiongqu Oxycholic acid 9.4Kg.

Embodiment 3

[0036] Replace the air in the hydrogenation reactor with nitrogen, add 200L of tert-butanol, stir and dissolve, then add 10Kg of 7-ketodeoxycholic acid, 4Kg of sodium carbonate, and 1g of 3# catalyst. After replacing the nitrogen in the reactor with hydrogen, keep the hydrogen pressure in the reactor at 5Mpa, and react at room temperature for 4 hours. Distill to remove the solvent in the reaction kettle, add 300L purified water, stir to dissolve, adjust PH3 with 1:3 hydrochloric acid, centrifuge, wash the filter cake with purified water until the pH of the washing water is greater than 5. Vacuum dry at 75°C until the water content is less than 0.5%, and obtain Xiongqu Oxycholic acid 9.6Kg.

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Abstract

The invention discloses a method for preparing an ursodesoxycholic acid by the chiral catalytic hydrogenation of a 7-ketodesoxycholic acid, which is characterized by comprising the following steps of: performing oxidation to prepare the 7-ketodesoxycholic acid from a chenodeoxycholic acid serving as an initiative raw material by using a common method; dissolving the 7-ketodesoxycholic acid into a solvent, adding a chiral catalyst, maintaining the pressure of 0 to 20 MPa under alkali condition, introducing nitrogen to perform hydrogenation reduction reaction at 10 to 80 DEG C, and performing distillation after the reaction is finished to remove the solvent; adding purified water in a volume which is 10 to 100 times that of a hydrogenation reduction reaction product, and adding acid liquor to crystallize the hydrogenation reduction reaction product; and separating solids from liquid, and performing washing and drying to obtain solid powder which is the ursodesoxycholic acid. The method for preparing the ursodesoxycholic acid by the chiral catalytic hydrogenation of the 7-ketodesoxycholic acid aims to overcome the shortcomings of the prior art, and ensures a short production flow, high yield and high quality.

Description

technical field [0001] The invention relates to a method for generating ursodeoxycholic acid by chiral catalytic hydrogenation of 7-ketodeoxycholic acid. Background technique [0002] At present, the starting materials for the synthesis of ursodeoxycholic acid at home and abroad are chenodeoxycholic acid and bovine cholic acid, and no matter what kind of raw material is used to synthesize ursodeoxycholic acid, it is necessary to first prepare 7-ketodeoxycholic acid , and then undergo hydrogenation reduction to obtain ursodeoxycholic acid. [0003] 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-ketodeoxycholic acid is reduced to ursodeoxycholic acid. 20% is reduced to chenodeoxycholic acid. After the reaction is completed, it needs to be separated and purified. The final ursodeoxycholic acid product is only about 60% of chenode...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
Inventor 秦和平张和平刘遗松黄凌霍延豪沈惠宾黄文军周海香梁待亮
Owner ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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