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A kind of synthetic method of deoxycholic acid

A technology of deoxycholic acid and a synthesis method, which is applied in the directions of steroids, organic chemistry, etc., can solve the problems of environmental pollution, complex process and high cost, and achieves the effects of strong reaction specificity, simple process and high yield.

Active Publication Date: 2015-10-14
ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The existing synthetic method is complicated in process, pollutes the environment, and the cost is relatively high, and the yield of deoxycholic acid is relatively low, so it is not suitable for industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] a. Preparation of methyl cholic acid: Dissolve 10 g of cholic acid in 50 ml of methanol, cool down to 5°C, add 0.1 ml of thionyl chloride, stir and react for 4 hours, solids precipitate out, filter, wash the filter cake with 10 ml of refrigerated methanol, and dry 9.8 g of methyl cholate was obtained.

[0033] b. Preparation of 3α, 12α-diacetylated-7α-hydroxycholate methyl ester; 8 g (0.0188 mol) of methyl cholate was dissolved in 50 ml of dichloromethane, and 5.75 g (0.0564 mol) of acetic anhydride and catalyst were added under stirring Mophenin 0.2g (0.0023mol), stirred at room temperature for 4h, then refluxed for 2h, added 30ml of water, layered, dichloromethane was concentrated until solids were precipitated, filtered to obtain 3α,12α-diacetylated-7α-hydroxycholic acid Methyl ester 9.3g;

[0034] c. Preparation of 3α, 12α-diacetylated-7-oxocholic acid methyl ester: Dissolve 9 g (0.0177 mol) of 3α, 12α-diacetylated-7α-hydroxycholic acid methyl ester in 50 ml of ter...

Embodiment 2

[0038] a. Preparation of methyl cholic acid: Dissolve 10 g of cholic acid in 20 ml of methanol, cool down to -15°C, add 1 ml of thionyl chloride, stir for 4 hours, and solids precipitate out, filter, wash the filter cake with 10 ml of frozen methanol, and dry 9.6 g of methyl cholate was obtained.

[0039] b. Preparation of 3α, 12α-diacetylated-7α-hydroxycholate methyl ester; 8 g (0.0188 mol) of methyl cholate was dissolved in 50 ml of dichloromethane, and 3.83 g (0.0376 mol) of acetic anhydride and catalyst were added under stirring Mopheneline 0.0654g (0.00075mol), stirring at room temperature for 2h, then reflux for 3h, add 35ml of water, separate layers, concentrate the dichloromethane phase until solid precipitates, filter to obtain 3α,12α-diacetylated group-7α-hydroxycholic acid Methyl ester 8.8g;

[0040] c. Preparation of 3α, 12α-diacetylated-7-oxocholic acid methyl ester: Dissolve 8 g (0.0157 mol) of 3α, 12α-diacetylated-7α-hydroxycholic acid methyl ester in 56 ml of ...

Embodiment 3

[0044]a. Preparation of methyl cholic acid: Dissolve 10 g of cholic acid in 100 ml of methanol, cool down to 25 ° C, add 0.5 ml of thionyl chloride, stir for 4 hours, and solids precipitate out, filter, wash the filter cake with 20 ml of frozen methanol, and dry 9.7 g of methyl cholate was obtained.

[0045] b. Preparation of 3α, 12α-diacetylated-7α-hydroxycholate methyl ester; 8 g (0.0188 mol) of methyl cholate was dissolved in 50 ml of dichloromethane, and 9.58 g (0.094 mol) of acetic anhydride and catalyst were added under stirring Mophenin 0.5g (0.00575mol), stirred at room temperature for 5h, then refluxed for 4h, added 50ml of water, layered, dichloromethane was concentrated until solid precipitated, filtered to obtain 3α,12α-diacetylated group-7α-hydroxycholic acid Methyl ester 16.5g;

[0046] c. Preparation of 3α,12α-diacetylated-7-oxocholic acid methyl ester: take 10g (0.01963mol) of 3α,12α-diacetylated-7α-hydroxycholic acid methyl ester and dissolve it in 70ml of te...

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Abstract

The invention discloses a synthetic method of deoxycholic acid. The method is characterized by comprising the following steps: (A) preparing cholate; (B) preparing 3 alpha, 12 alpha-diacetyl base-7 alpha-hydroxyl cholate; (C) preparing 3 alpha, 12 alpha-diacetyl base-7-oxocholate; (D) preparing 7-oxocholic acid; and (E) preparing deoxycholic acid. The purpose of the invention is to provide the synthetic method of the deoxycholic acid with simple process, comparatively lower production cost, high deoxycholic acid yield and convenience in industrial production in order to overcome defects in the prior art. By using cholic acid as a raw material and selecting thionyl chloride, morpholine and ammonium chloride as catalysts, the synthetic method of the deoxycholic acid, disclosed by the invention, has the advantages of simplicity in process, strong reaction specificity, high yield and great convenience in industrial production. Through adoption of the synthetic method disclosed by the invention, the deoxycholic acid is prepared with low cost.

Description

technical field [0001] The invention relates to a synthesis method of deoxycholic acid, that is, a synthesis method of 3α, 12α-dihydroxy-5β-cholanic acid, which belongs to the field of organic chemical synthesis. Background technique [0002] Deoxycholic acid (3α, 12α-dihydroxy-5β-cholanic acid) deoxycholic acid, also known as deoxycholic acid (DCA for short), is a bile acid that lacks a hydroxyl group on C-7. A free bile acid derived from an atom, which mainly exists in the form of taurine and glycine in the bile, and has the effect of promoting bile secretion and anti-inflammation clinically. [0003] Deoxycholic acid is also mainly used in biochemical research, bacteriology and enzymatic research; as a lipase accelerator and anion remover, for the dissolution of proteins, and for the preparation of bacterial culture media. [0004] Deoxycholic acid can be made into various deoxycholate salts, which are mainly used in various preparations, such as tablets, injections and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J9/00
Inventor 黄文军张和平刘遗松刘骅霍延豪阮宇峰梁待亮沈惠宾周海香邱国华
Owner ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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