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Method for preparing ursodesoxycholic acid by electro-reduction

A technology of ursodeoxycholic acid and ketolithocholic acid, which is applied in the field of electroreduction to prepare ursodeoxycholic acid, can solve problems such as high technical requirements and unsafety, and achieve simplified process flow, basic environment and no environmental pollution Effect

Active Publication Date: 2012-09-12
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The foreign existing technology uses sodium or potassium in ethanol solvent to reduce 7-ketolithocholic acid (7K-LCA) to produce ursodeoxycholic acid, but the technical requirements are high, and this method is widely used in industry. Hazardous chemicals like these are quite unsafe
At present, there are relatively few reports on the preparation of ursodeoxycholic acid by electrochemical methods, and the published patents are only preliminary laboratory studies.

Method used

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  • Method for preparing ursodesoxycholic acid by electro-reduction
  • Method for preparing ursodesoxycholic acid by electro-reduction
  • Method for preparing ursodesoxycholic acid by electro-reduction

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preparation example Construction

[0020] In order to study a green and pollution-free method for preparing ursodeoxycholic acid, the inventors of the present invention have studied a simple and easy method for preparing ursodeoxycholic acid through extensive and in-depth research in electrochemical aspects. The method has the advantages of simple process, mild operating conditions, safety and environmental protection.

[0021] See Figure 1-3 As shown, the method for preparing ursodeoxycholic acid by electroreduction of the present invention is to mix an organic solution of 7-ketolithocholic acid and an aqueous solution of potassium bromide in the diaphragm electrolyzer 7 as the catholyte 5, and the catholyte Solution 5 is a catholyte with a concentration of 7-ketolithocholic acid between 11.54 and 21.23 mg / mL and a concentration of potassium bromide between 0.03mol / L and 0.13mol / L, wherein the 7-ketolithocholic acid is organic The volume ratio of the organic solvent in the solution to the water in the potass...

example 1

[0031] Dissolve 0.75g of 7-ketolithocholic acid (prepared according to Chinese patent application CN200610029416.1, invention name: a preparation method for 7-ketolithocholic acid) in 50mL of anhydrous methanol, and dissolve 0.7735g of potassium bromide Dissolve in 15mL deionized water, and then mix the two evenly as catholyte 5. 25% dilute sulfuric acid was used as the anolyte6. The effective electrode area is 5×3cm 2 , the current density is 20A / m 2 , the temperature of the water bath was set to 50°C, and the power-on time was 22h. After the reaction, the catholyte 5 was rotary evaporated to solid, added alkali solution to dissolve, then adjusted the pH to 2.0 with hydrochloric acid, filtered and dried the filter cake to obtain the product. The content of UDCA detected by HPLC was 46%.

example 2

[0033] Dissolve 2.46g of 7-ketolithocholic acid (prepared according to Chinese patent application CN200610029416.1, invention name: a preparation method for 7-ketolithocholic acid) in 140mL of anhydrous methanol, and dissolve 0.5748g of potassium bromide Dissolve in 21mL deionized water, and mix the two evenly as catholyte 5. Use 10% dilute hydrochloric acid as the anolyte6. The effective electrode area is 5×3cm 2 , the current density is 10A / m 2, the temperature of the water bath was set to 70°C, and the reaction time was 24h. After the reaction, the catholyte 5 was rotary evaporated to solid, added alkali solution to dissolve, then adjusted the pH to 2.0 with hydrochloric acid, filtered and dried the filter cake to obtain the product. The content of UDCA detected by HPLC was 40%.

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Abstract

The invention relates to a method for preparing ursodesoxycholic acid by electro-reduction, which comprises the steps of: in a diaphragm electrolytic cell, evenly mixing 7-ketone liithocholic acid organic solution and potassium bromide water solution to be taken as catholyte, wherein in the catholyte, the concentration of 7-ketone liithocholic acid is within the range of 11.54-21.23mg / mL, the concentration of potassium bromide is within the range of 0.03-0.13mol / L, the volume ratio between an organic solvent in the 7-ketone liithocholic acid organic solution and water in the potassium bromide water solution is not less than 10: 3, acid solution is anolyte, the concentration of acid solution is within the range of 1-25%, and the active electrode area is 5*3 cm<2>; carrying out electrolysis by constant current, wherein the density of the constant current is within the range of 10-30A / m<2>, and the electrolytic temperature is 25-70 DEG C; and preferentially, after the electrolysis by the constant current, carrying out rotary evaporation on catholyte until that solid forms, adding alkali liquor for dissolving, adjusting the pH value to be 2.0, filtering and drying a filter cake. The method for preparing the ursodesoxycholic acid by the electro-reduction not only simplifies the process flow in the industrial production and reduces the production cost, but also is safe and environment-friendly, thus being suitable for large-scale popularization and application.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to the technical field of organic electrosynthesis, in particular to a method for preparing ursodeoxycholic acid through electroreduction. Background technique [0002] Ursodeoxycholic acid (UDCA) is the main active ingredient of bear bile, a precious traditional Chinese medicine, and it is a drug for treating primary biliary cirrhosis (PBC). Clinical application at home and abroad proves that ursodeoxycholic acid has a good curative effect in treating various gallbladder diseases, liver diseases and various hyperlipidemia diseases, especially in dissolving cholesterol gallstones. In recent years, some new curative effects have been discovered. Such as cell protection, immune regulation and so on. "Chinese Pharmacopoeia" 2005 edition (Part II) classifies it as a gallstone-dissolving drug, and "National Essential Drugs List (Equipment and Use Part of Primary Medical and H...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/04C25B9/10C25B3/25C25B9/23
Inventor 曹学君袁向玺
Owner EAST CHINA UNIV OF SCI & TECH
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