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Preparation method of chenodeoxycholic acid

A technology of chenodeoxycholic acid and hyodeoxycholic acid, which is applied in the field of preparation of hyodeoxycholic acid to synthesize chenodeoxycholic acid, can solve the problems of unfavorable large-scale production and harshness, and achieve the reduction of the proportion of side reactions and accurate The effect of high degree and high yield

Active Publication Date: 2017-06-13
眉山市新功生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method uses potassium-liquid ammonia alkali metal reduction to construct the 7β-OH configuration, which requires low-temperature reaction, the conditions are harsh, and the operation remains unchanged, which is not conducive to large-scale production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1. Refined Hyodeoxycholic Acid

[0043] Take 100g of common commercially available hyodeoxycholic acid (hyodeoxycholic acid content 72.6%), add 2 times the volume of ethyl acetate 200mL, heat and reflux for 1 hour, slowly stir and cool down to 0-5°C, crystallize for 2 hours, and filter to obtain the content 94.7% hyodeoxycholic acid 61.7g.

[0044] 2. Methyl esterification to protect the carboxyl group

[0045]Take 50g of refined hyodeoxycholic acid, add 2 times the volume of methanol 100mL, 1g of methanesulfonic acid, stir and react at 25-30°C for 4 hours, HPLC confirms that the reaction rate is above 98%, and recover methanol under normal pressure below 80°C. Add 5 times the volume of toluene 250mL, heat to 70°C, stir for 1 hour, then add 5 times the volume of 2% sodium carbonate solution, stir and react for 1 hour, let stand to separate the lower water layer, vacuumize and heat to recover toluene, and obtain hyodeoxygen Cholic acid methyl ester 50.5g.

[0046] Eli...

Embodiment 2

[0051] 1. Refined Hyodeoxycholic Acid

[0052] Take 100g of common commercially available hyodeoxycholic acid (hyodeoxycholic acid content 73.0%), add 2 times the volume of ethyl acetate 200mL, heat and reflux for 1 hour, slowly stir and cool down to 0-5°C, crystallize for 2 hours, and filter to obtain the content 94.9% hyodeoxycholic acid 61.8g.

[0053] 2. Methyl esterification to protect the carboxyl group

[0054] Take 50g of refined hyodeoxycholic acid, add 150mL of 3 times the volume of methanol, 1g of methanesulfonic acid, stir and react at 25-30°C for 4 hours, HPLC confirms that the reaction rate is above 98%, and the methanol is recovered under normal pressure below 80°C. Add 5.6 times the volume of toluene 280mL, heat to 65°C, stir for 1 hour, then add 5 times the volume of 2% sodium carbonate solution, stir and react for 1 hour, let stand to separate the lower water layer, vacuumize and heat to recover the toluene, and obtain hyodeoxygen Cholic acid methyl ester 5...

Embodiment 3

[0060] 1. Refined Hyodeoxycholic Acid

[0061] Take 100g of common commercially available hyodeoxycholic acid (hyodeoxycholic acid content 73.5%), add 2 times the volume of ethyl acetate 200mL, heat and reflux for 1 hour, slowly stir and cool down to 0-5°C, crystallize for 2 hours, and filter to obtain the content 95.2% hyodeoxycholic acid 60.9g.

[0062] 2. Methyl esterification to protect the carboxyl group

[0063] Take 50g of refined hyodeoxycholic acid, add 2 times the volume of methanol 100mL, 1g of methanesulfonic acid, stir and react at 25-30°C for 4 hours, HPLC confirms that the reaction rate is above 98%, and recover methanol under normal pressure below 80°C. Add 6 times the volume of toluene 300mL, heat to 70°C, stir for 1 hour, then add 5 times the volume of 2% sodium carbonate solution, stir and react for 1 hour, let stand to separate the lower water layer, vacuumize and heat to recover toluene, and obtain hyodeoxygen Cholic acid methyl ester 50.1g.

[0064] El...

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Abstract

The invention discloses a preparation method of chenodeoxycholic acid. The preparation method includes following steps: refining hyodeoxycholic acid; preparing a methyl hyodeoxycholate; eliminating 6-bit hydroxyl; preparing chenooxycholic acid. The preparation method is simple in steps, raw materials used in the method are wide and sufficient in source, and the preparation method is high in yield of the chenodeoxycholic acid.

Description

technical field [0001] The invention relates to the field of biomedicine, in particular to a preparation method for synthesizing chenodeoxycholic acid from hyodeoxycholic acid. Background technique [0002] The main function of chenodeoxycholic acid (CDCA) is to reduce the saturation of cholesterol in the bile. After the vast majority of patients take CDCA, when CDCA accounts for 70% of the bile salt in the bile, the lipids return to the state of micelles, and the cholesterol is in the state of micelles. unsaturated state, so that the cholesterol in the stones dissolves and falls off. Large doses of CDCA can inhibit the synthesis of cholesterol and increase the secretion of bile in patients with cholelithiasis, but the secretion of bile salts and phospholipids remains unchanged. In addition, chenodeoxycholic acid is a raw material for the synthesis of ursodeoxycholic acid and other steroidal compounds. As an epimer of ursodeoxycholic acid, its artificial synthesis has also ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCC07J9/005
Inventor 梁万超蒋先曲
Owner 眉山市新功生物科技有限公司
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