Method for preparing chenodeoxycholic acid from seal cholic acid

A technology of chenodeoxycholic acid and cholic acid, applied in the field of chenodeoxycholic acid, can solve problems such as waste, achieve the effects of avoiding biological waste pollution, alleviating insufficient supply, good economic value and application prospects

Inactive Publication Date: 2021-02-09
苏州恩泰新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, duck bile is mainly used to extract CDCA, but PCA is generally left in the residual bile paste waste, which is generally used as

Method used

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  • Method for preparing chenodeoxycholic acid from seal cholic acid
  • Method for preparing chenodeoxycholic acid from seal cholic acid
  • Method for preparing chenodeoxycholic acid from seal cholic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] (1) Preparation of compound ii

[0041] N 2 Under protection, PCA (600 g, 1.47 mol) and N,N-diisopropylethylamine (341.6 g, 2.64 mol) were added into 12 L of dichloromethane with stirring started. The temperature was lowered to 0-5°C, and methylsulfonyl chloride (185 g, 1.61 mol) was added dropwise. After the dropwise addition, continue to keep stirring for 8h. After adding 2L of water and stirring, the liquid was separated, and the organic phase was washed once with 3.1L of saturated ammonium chloride aqueous solution, dried by adding anhydrous sodium sulfate, and concentrated to obtain 764.7g of compound ii.

[0042] 1 HNMR (400MHz, DMSO) δ12.61(s, 1H), 5.42(m, 1H), 4.34(d, 1H), 4.16(d, 1H), 3.60(m, 1H), 3.17(m, 1H), 3.10(s, 3H), 1.15-1.8(m, 24H), 1.09(d, 3H), 0.99(s, 3H), 0.59(s, 3H)

[0043] (2) Preparation of compound iii

[0044] Compound ii (764.7 g, 1.47 mol) and lithium bromide monohydrate (462.4 g, 4.41 mol) obtained in the previous step were added to 7....

Embodiment 2

[0054] (1) Preparation of compound ii

[0055] N 2 Under protection, PCA (0.97 kg, 2.37 mol) and diazabicyclo (722 g, 4.74 mol) were added into 15 L of tetrahydrofuran and stirred. Cool down to 0-5°C, p-toluenesulfonyl chloride (472.81g, 2.48mol). After the dropwise addition, continue to keep stirring for 10 h. Add 2L of ethyl acetate and 5L of water for extraction and separation. The organic phase was washed once with 5 L of saturated aqueous ammonium chloride solution, dried by adding anhydrous sodium sulfate, and then concentrated to obtain 1.41 kg of compound ii.

[0056] 1 HNMR (400MHz, DMSO) δ12.84(s, 1H), 7.89(d, 2H), 7.38(d, 2H), 5.44(m, 1H), 4.36(d, 1H), 4.17(d, 1H), 3.65(m, 1H), 3.21(m, 1H), 2.43(s, 3H), 0.9-1.9(m, 24H), 1.12(d, 3H), 0.98(s, 3H), 0.59(s, 3H)

[0057] (2) Preparation of compound iii

[0058] Compound ii (1.41kg, 2.37mol) and sodium bromide (610.1g, 5.93mol) were added to 10L acetone and refluxed for 24h. After concentration under reduced press...

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Abstract

The invention provides a method for preparing chenodeoxycholic acid CDCA by taking seal cholic acid as a raw material, on one hand, an application is found for seal cholic acid, and on the other hand,a new raw material source is provided for chenodeoxycholic acid, so that the problem of supply shortage of chenodeoxycholic acid crude drugs can be partially relieved, meanwhile, the problem of corresponding biological waste pollution is avoided, the problem of industrial production is well solved, and the method has very good economic value and application prospect.

Description

technical field [0001] The invention relates to a method for chenodeoxycholic acid, in particular to a method for preparing chenodeoxycholic acid from seal cholic acid. Background technique [0002] Cholesteric acid is a polyhydroxy steroidal carboxylic acid compound extracted from biological bile cream, among which ursodeoxycholic acid (UDCA) and chenodeoxycholic acid (CDCA) are more important. This type of compound has strong pharmacological properties and has a good curative effect on gallstones and other hepatobiliary diseases, and is one of the most widely used drugs for treating gallstones in the world. At present, CDCA is an important raw material for the artificial preparation of UDCA and other steroid drugs. It is in great demand and has been in short supply. It is urgent to solve the problem of the source of product supply. [0003] Duck bile is one of the most important domestic sources of CDCA. Long Kanghou and others studied the components of cholesteric acid ...

Claims

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Application Information

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IPC IPC(8): C07J9/00
CPCC07J9/005
Inventor 王飞袁海涛
Owner 苏州恩泰新材料科技有限公司
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