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Preparation method of 7-keto lithocholic acid

A kind of ketolithocholic acid, said technology, applied in the field of preparation of 7-ketolithocholic acid, can solve the problems of harsh operating conditions, low efficiency, difficult product separation, etc., and achieve the effect of mild operating conditions

Inactive Publication Date: 2012-09-05
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of this, if the electrochemical synthesis method can be used to prepare 7-ketolithocholic acid, it will overcome the existing ursodeoxycholic acid preparation method with long preparation steps, low efficiency, difficult product separation, harsh operating conditions and easy Disadvantages such as polluting the environment

Method used

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  • Preparation method of 7-keto lithocholic acid
  • Preparation method of 7-keto lithocholic acid
  • Preparation method of 7-keto lithocholic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Dissolve 0.4g KBr in 13ml secondary deionized water, weigh 2.0g CDCA and dissolve it in 50ml acetonitrile, mix the two solutions evenly and put them into the anode chamber of the H-type diaphragm electrolyzer as the anolyte. Take 63ml of 20% dilute sulfuric acid as catholyte. HF-101 strong acid type cation exchange membrane is the diaphragm. with PbO 2 The / Ti mesh electrode is the anode, and the stainless steel plate is the cathode. The current density used is 95.2A / m 2, as detected by TLC, when CDCA basically reacted, the electrolysis was stopped, and the power-on time was 2.5h. 1.697 g of crude 7K-LCA was obtained, and the HPLC content was 90.4%. The calculated yield and current efficiency were 77.1% and 84.2%, respectively. After the product was purified by column chromatography and recrystallization, the melting point was measured: m.p. 200-203°C (literature value: 201-203°C). 1H NMR analysis results: δ0.5~1.8, 2.1, 2.2 (33H, m, -CH 2 -, -CH 2 CH 3 ,-CH 2...

Embodiment 2

[0032] Dissolve 0.4g KBr in 13ml secondary deionized water, weigh 2.0g CDCA and dissolve it in 50ml ethanol, mix the two solutions evenly and put them into the anode chamber of the H-type diaphragm electrolyzer as the anolyte. Use 63ml of 20% dilute sulfuric acid as catholyte. HF-101 strong acid type cation exchange membrane is the diaphragm. with PbO 2 The / Ti mesh electrode is the anode, and the stainless steel plate is the cathode. The current density used is 95.2A / m 2 , as detected by TLC, when CDCA basically reacted, stop the electrolysis, and the power-on time was about 4.5h. 1.652 g of crude 7K-LCA was obtained, with an HPLC content of 89.5%. The calculated yield and current efficiency were 74.3% and 45.5%, respectively. After the product is purified, the melting point is measured: m.p.200-203°C (literature value: 201-203°C).

Embodiment 3

[0034] Dissolve 0.4g KBr in 13ml secondary deionized water, weigh 2.0g CDCA and dissolve it in 50ml acetonitrile, mix the two solutions evenly and put them into the anode chamber of the H-type diaphragm electrolyzer as the anolyte. Use 63ml of 20% dilute sulfuric acid as catholyte. HF-101 strong acid type cation exchange membrane is the diaphragm. with PbO 2 The / Ti mesh electrode is the anode, and the stainless steel plate is the cathode. The current density used is 190.4A / m 2 , as detected by TLC, when CDCA basically reacted, the electrolysis was stopped, and the power-on time was 2.25h. 1.423 g of crude 7K-LCA was obtained, with an HPLC content of 87.9%. The calculated product yield and current efficiency were 62.8% and 38.1%, respectively. After the product is purified, the melting point is measured: m.p.200-203°C (literature value: 201-203°C).

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Abstract

The invention relates to 7-alkone lithocholic acid preparing method. It includes the following steps: dissolving the compound into the organic solvent to form electrolyte, electrolyzing the electrolyte by constant current at oxidizing medium condition to gain the object. The electrolyzing current density is 47.6A / m<2>-190.4A / m<2>. The invention has the advantages of moderate operation condition, green, simplifying ursodesoxycholic acid preparing steps.

Description

technical field [0001] The invention relates to a preparation method of 7-ketolithocholic acid, in particular to a method for preparing 7-ketolithocholic acid by electrolysis. Background technique [0002] 7-Ketolithocholic acid [7K-LCA, whose structure is shown in formula (1)] is an important intermediate for the preparation of ursodeoxycholic acid (UDCA). 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 bear bile, a precious traditional Chinese medicine. However, bear bile is a very scarce resource, which is difficult to meet the needs of clinical application. [0003] [0004] 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 c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/02C25B3/23
Inventor 曹学君晋永红
Owner EAST CHINA UNIV OF SCI & TECH
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