Stereoselective method for preparing ursodeoxycholic acid

A technology of ursodeoxycholic acid and stereoselectivity, which is applied in the direction of electrolysis process, electrolysis components, electrolysis organic production, etc., can solve the problems of immature electrochemical synthesis methods, achieve high-efficiency preparation, high conversion rate, and short preparation steps Effect

Active Publication Date: 2017-11-28
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the current electrochemical synthesis method is still immature

Method used

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  • Stereoselective method for preparing ursodeoxycholic acid
  • Stereoselective method for preparing ursodeoxycholic acid
  • Stereoselective method for preparing ursodeoxycholic acid

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Experimental program
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Effect test

Embodiment 1

[0027] Dissolve 0.3g KBr in 12ml of water, 2.0g of 7-ketolithocholic acid in 110ml of methanol, and add 10ml of dimethylformamide, then mix the two solutions into the cathode cell as the catholyte; 10% dilute sulfuric acid is used as the anolyte; the lead electrode is used as the cathode, and the ruthenium-titanium electrode network is used as the anode; the HF101 strong-acid cation exchange membrane is used as the diaphragm, and the water bath is 50°C, and the constant current is electrolyzed, and the current density is 85A m -2 , Stop electrolysis when 7K-LCA disappears after thin layer chromatography. 1.932 g of UDCA crude product was obtained, the conversion rate by HPLC was 89.1%, and the purity was 52.3%.

Embodiment 2

[0029] Dissolve 0.3g KBr in 12ml water, dissolve 2.0g 7-ketolithocholic acid in 110ml methanol and add 5ml dimethyl sulfoxide, then mix the two solutions and put them into the cathode cell as catholyte; 5% dilute sulfuric acid is used as the anolyte; the lead electrode is used as the cathode, the ruthenium-titanium electrode network is used as the anode; the HF101 strong acid type cation exchange membrane is used as the diaphragm, the water bath is 65°C, and the constant current is electrolyzed, and the current density is 82A m -2 , Stop electrolysis when 7K-LCA disappears after thin layer chromatography. 1.894 g of crude UDCA was obtained, the conversion rate was 88.2% and the purity was 78.7% as measured by HPLC.

Embodiment 3

[0031] Dissolve 0.3g KBr in 12ml water, dissolve 2.5g 7-ketolithocholic acid in 110ml ethanol and add in 3ml dimethylacetamide, then mix the two solutions and put them into the cathode cell as catholyte; The 5% dilute sulfuric acid is used as the anolyte; the lead electrode is used as the cathode, and the PbO2 / Ti electrode mesh is used as the anode; the HF101 strong acid type cation exchange membrane is used as the diaphragm, and the water bath is 60°C, and the constant current is electrolyzed, and the current density is 85A m -2, Stop electrolysis when 7K-LCA disappears after thin layer chromatography. 1.914 g of crude UDCA was obtained, the conversion rate of the raw material detected by HPLC was 74.3%, and the purity was 55.1%.

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Abstract

The invention relates to a method for stereoselectively preparing ursodeoxycholic acid, which is characterized in that it comprises the following steps: step (1): dissolving the compound of formula (I) in a mixed solution of an organic solvent and a stereoselective reagent The electrolyte is prepared, and the compound structure of the formula (I) is as follows: Step (2): In the presence of the stereoselective reagent, the electrolyte is subjected to a current density of 75A·m -2~100A·m-2 Under constant current reduction, obtain the solution containing ursodeoxycholic acid of formula (II), the structural formula of ursodeoxycholic acid of described formula (II) is as follows: The method for stereoselectively preparing ursodeoxycholic acid can obtain ursodeoxycholic acid with higher purity, and has high yield, short preparation steps, high efficiency, simple operating conditions and no environmental pollution.

Description

technical field [0001] The invention relates to the field of preparation of medicines by electrochemical reduction, in particular to the artificial synthesis of natural medicines, in particular to a method for electrochemical stereoselective preparation of ursodeoxycholic acid. Background technique [0002] Ursodeoxycholic acid is mainly used to treat various diseases such as gallstones, cholecystitis, hepatitis and hyperlipidemia, and is the only drug approved by the FDA for the treatment of primary biliary cirrhosis (PBC). Ursodeoxycholic acid is the main active ingredient of the precious traditional Chinese medicine bear bile. However, bear bile is a very scarce resource, which is difficult to meet the needs of clinical application. Since the 1950s, there have been chemical synthesis methods using animal bile acids as raw materials. Japanese patent (JP 0161496) reported that taking bovine and sheep cholic acid as raw materials, selectively protecting the 3-position hydr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/04C25B3/25
Inventor 曹学君黄晓梅董东东
Owner EAST CHINA UNIV OF SCI & TECH
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