Process for preparing deoxycholic acid

A technology of ursodeoxycholic acid and chenodeoxycholic acid, which is applied in the field of preparation of ursodeoxycholic acid, can solve the problems of high energy consumption for solvent recovery, violent reaction, and many steps, and achieve low equipment investment and simple process flow , the effect of less chemical reagents

Active Publication Date: 2014-12-10
HARBIN INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In principle, the aforementioned processes can produce ursodeoxycholic acid, but the 7-step or 2-step process first oxidizes chenodeoxycholic acid to 7-ketolithocholic acid, and then reduces it to ursodeoxycholic a

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Take 1000g of chenodeoxycholic acid as the raw material and dissolve it evenly with 3-50L of isopropanol;

[0027] (2) Add 10-150g (1R, 3S)-(+)-camphoric acid and 5-20g aluminum oxide powder to the above solution, stir and react at 25-60°C and 60-120r / min for 10 -30min, stand still for 3-12h, 3α-hydroxyl generates derivatives;

[0028] (3) Add 0.5-3.0L bis(2-methoxyethoxy)aluminum dihydrogen sodium, 0.1-1.2g anilinomethylpyrrolidine and 0.2-5L tert-butanol to the above solution system, pressurize with hydrogen To 0.5-3MPa, under the condition of temperature 25-60℃, microwave frequency 300-800MHz, power 50-200W, irradiate for 1-6h, 7α-hydroxyl is converted to 7β-hydroxyl;

[0029] (4) Cool the above system to normal temperature, reduce the pressure to normal pressure, filter out the solid matter with a filter with a pore size of 0.5-1.5 μm, and collect the filtrate;

[0030] (5) Add 50-200L of pure water to the filtrate and adjust the acidity to pH = 2-3 with hydro...

Embodiment 2

[0033] (1) Take 1000g of chenodeoxycholic acid as the raw material and dissolve it evenly with 25L of isopropanol;

[0034] (2) Add 50g (1R,3S)-(+)-camphoric acid and 10g aluminum oxide powder to the above solution, stir and react at 40°C and 80r / min for 20min, stand still for 6h, 3α-hydroxyl is formed derivative;

[0035] (3) Add 1.5L bis(2-methoxyethoxy)aluminum dihydrogen sodium, 0.5g anilinomethylpyrrolidine and 1.5L tert-butanol to the above solution system, pressurize to 1.5MPa with hydrogen, and Under the conditions of temperature 30°C, microwave frequency 500MHz, and power 100W, irradiate for 4 hours, and the 7α-hydroxyl group is converted into 7β-hydroxyl group;

[0036] (4) Cool the above system to normal temperature, reduce the pressure to normal pressure, filter out the solid matter with a filter with a pore size of 1.5 μm, and collect the filtrate;

[0037] (5) Add 100L of pure water to the filtrate and adjust the acidity to pH = 2.5 with hydrochloric acid, let ...

Embodiment 3

[0040] (1) Take 1000g of chenodeoxycholic acid as the raw material and dissolve it evenly with 3-5L cycloethanol;

[0041] (2) Add 5-50g of S-(+)mandelic acid and 5-15g of vanadium pentoxide powder, stir and react for 30-180min at 25-75℃, speed 60-180r / min, stand still for 1-6h, 3α - hydroxyl generating derivatives;

[0042](3) Add 0.5-5.0L bis(2-methoxyethoxy) aluminum dihydrogen sodium, 0.1-1.0g anilinomethylpyrrolidine and 0.5-10L tert-butanol to the above solution system, pressurize with hydrogen To 0.5-2MPa, under the conditions of temperature 35-80℃, microwave frequency 300-1000MHz, power 100-1500W, irradiate for 2-6h, 7α-hydroxyl is converted to 7β-hydroxyl;

[0043] (4) Cool the above system to normal temperature, reduce the pressure to normal pressure, filter out the solid matter with a filter with a pore size of 0.5-1.5 μm, and collect the filtrate;

[0044] (5) Add 50-200L of pure water to the filtrate and adjust the acidity to pH = 2-3 with hydrochloric acid or s...

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Abstract

The invention discloses a process for preparing deoxycholic acid. The process comprises the following steps: (1) by taking chenodeoxycholic acid as a raw material, adding a proper solvent; (2) adding a reagent and a catalyst, and selectively generating a derivative together with 3alpha-hydroxyl; (3) adding a chiral inducer, an asymmetric synthesis catalyst, tertiary butanol or octyl pentanol, filling hydrogen and pressurizing, converting 7alpha-hydroxyl in the chenodeoxycholic acid into 7beta-hydroxyl through one step under radiation conditions, thereby generating a coarse product of chenodeoxycholic acid; (4) washing the coarse product of chenodeoxycholic acid, filtering and removing impurities; (5) selecting a corresponding solvent, and extracting to remove the unreacted chenodeoxycholic acid and other impurities; and (6) drying the chenodeoxycholic acid, and collecting and packaging to obtain a finished product. The process flow is simple, the equipment investment is low, fewer chemical reagents are used, the conversion rate is high, raw materials are fully utilized, the production efficiency is improved, the production cost and the energy consumption are greatly reduced, and the process is suitable for industrial production.

Description

technical field [0001] The invention relates to a process for preparing biochemicals, in particular to a process for preparing ursodeoxycholic acid. Background technique [0002] Ursodeoxycholic acid is one of the main active ingredients in bear bile. It is clinically used to dissolve gallstones, and it also has certain effects on toxic hepatitis, cholecystitis, primary sclerosing cholangitis, and primary cholestatic cirrhosis. treatment effect. [0003] Ursodeoxycholic acid can be extracted and isolated from bear bile, or synthesized by biosynthesis. [0004] Since 1955, Kanazawa proposed to use cholic acid as a raw material for the synthesis of ursodeoxycholic acid in 7 steps. In 1984, Giordano et al., UP4486352, Kimura et al. Oxycholic acid process has been improved, using alkali metal as reducing agent. [0005] Bharucha et al. in 1985, US4547271, Hatsutori et al. in 1994, and JP6002184 respectively proposed the process of preparing ursodeoxycholic acid by electrochem...

Claims

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Application Information

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IPC IPC(8): C07J9/00
Inventor 徐华民
Owner HARBIN INST OF TECH
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