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Preparation method of 3Alpha-hydrol-7-oxo-5Beta-cholanic acid

A technology of cholanoic acid and chenodeoxycholic acid, which is applied in the directions of steroids and organic chemistry, can solve the problems of difficult combination and optimization, poor compatibility with organic solvents, poor selectivity, etc., and achieves broad development and application prospects. The effect of mild reaction conditions and easy operation

Inactive Publication Date: 2016-06-15
SUZHOU JINGYE MEDICINE & CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above methods have the following disadvantages: (1) the N-bromosuccinimide oxidation method produces more organic wastewater, and it is difficult to control the end point of the oxidation reaction; (3) The compatibility between sodium hypochlorite aqueous solution and raw materials and organic solvents is poor, which is not conducive to the progress of the reaction; (4) The electrochemical oxidation method requires a special type of electrolytic cell, and these electrolytic cells are mostly non-standard equipment. Processing and procurement are difficult, and the reaction process is affected by various factors such as current, voltage, electrode material, acid, alkali, solvent type, temperature, etc., and it is difficult to combine and optimize

Method used

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  • Preparation method of 3Alpha-hydrol-7-oxo-5Beta-cholanic acid
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  • Preparation method of 3Alpha-hydrol-7-oxo-5Beta-cholanic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Example 1: Preparation and purification of 3α-hydroxy-7-oxo-5β-cholanic acid.

[0032] (1) Preparation of 3α-hydroxy-7-oxo-5β-cholanic acid:

[0033] Add chenodeoxycholic acid (50g), methanol (300g) and citric acid (5g) into a three-necked flask, heat to 50°C under mechanical stirring, and keep it for 30min; after cooling to 5°C, add hydrogen peroxide solution dropwise ( 16g, 28wt%), and the dropping temperature was controlled within 15°C. After the dropwise addition was completed, the temperature was kept at 10°C for 5 hours; after the heat preservation reaction was completed, methanol (200g) was recovered and water (500g) was added, stirred for 2 hours, and filtered , washed with water, and dried to obtain a crude product of 3α-hydroxy-7-oxo-5β-cholanic acid.

[0034] (2) Purification of 3α-hydroxy-7-oxo-5β-cholanic acid:

[0035] Add the crude product prepared in step (1) to a mixed solvent of isopropanol and ethyl acetate (isopropanol: ethyl acetate = 1:3 (v / v)), ...

Embodiment 2

[0036] Example 2: Preparation and purification of 3α-hydroxy-7-oxo-5β-cholanic acid.

[0037] (1) Preparation of 3α-hydroxy-7-oxo-5β-cholanic acid:

[0038] Add chenodeoxycholic acid (80g), ethanol (640g) and tartaric acid (8g) into a three-necked flask, heat to 45°C under mechanical stirring, and keep it for 30min; after cooling to 5°C, add dropwise hydrogen peroxide aqueous solution (26g , 28wt%), and the dropping temperature was controlled within 15°C. After the dropwise addition was completed, the reaction was incubated at 11°C for 4h; Washed with water and dried to obtain the crude product of 3α-hydroxy-7-oxo-5β-cholanic acid.

[0039] (2) Purification of 3α-hydroxy-7-oxo-5β-cholanic acid:

[0040] Add the crude product prepared in step (1) to a mixed solvent of isopropanol and ethyl acetate (isopropanol: ethyl acetate = 1:3 (v / v)), heat and reflux for 30 minutes under mechanical stirring; the reflux is completed Finally, add activated carbon for decolorization and fil...

Embodiment 3

[0041] Example 3: Preparation and purification of 3α-hydroxy-7-oxo-5β-cholanic acid.

[0042] (1) Preparation of 3α-hydroxy-7-oxo-5β-cholanic acid:

[0043] Add chenodeoxycholic acid (130g), isopropanol (900g) and sulfuric acid (13g) into a three-necked flask, heat to 30°C under mechanical stirring, and keep it for 1h; after cooling to 2°C, add hydrogen peroxide solution dropwise (42g, 28wt%), and the dropping temperature was controlled within 15°C. After the dropwise addition was completed, the reaction was incubated at 12°C for 3h; Filter, wash with water, and dry to obtain the crude product of 3α-hydroxy-7-oxo-5β-cholanic acid.

[0044] (2) Purification of 3α-hydroxy-7-oxo-5β-cholanic acid:

[0045] Add the crude product prepared in step (1) to a mixed solvent of isopropanol and ethyl acetate (isopropanol: ethyl acetate = 1:3 (v / v)), heat and reflux for 30 minutes under mechanical stirring; the reflux is completed Finally, add activated carbon for decolorization and filter...

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Abstract

The invention discloses a preparation method of 3α-hydroxy-7-oxo-5β-cholanic acid. Specifically, the preparation method of the present invention uses hydrogen peroxide as an oxidizing agent to oxidize chenodeoxycholic acid with the participation of an acid catalyst to obtain 3α-hydroxy-7-oxo-5β-cholanic acid, wherein chenodeoxycholic acid The mass ratio between acid and hydrogen peroxide is 1:0.05~0.15. The preparation method of the invention has the characteristics of mild and safe reaction conditions, simple and controllable operation, low cost, high yield, low pollution, etc., and has broad development and application prospects.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of 3α-hydroxyl-7-oxo-5β-cholanic acid. Background technique [0002] Information about 3α-hydroxy-7-oxo-5β-cholanic acid is as follows: [0003] Chinese name: 3α-hydroxy-7-oxo-5β-cholic acid, also known as 7-ketolithocholic acid (7-Ketolithocholic acid) or 7-oxolithocholic acid (7-Oxolithocholacid); [0004] English name: 3-Alpha-hydroxy-7-oxo-5-beta-cholanic acid; [0005] CAS: 4651-67-6; [0006] Structural formula: [0007] Molecular formula: C 24 h 38 o 4 ; [0008] Molecular weight: 390.56; [0009] Properties: white crystalline powder; odorless; insoluble in water, soluble in alcohol. [0010] 3α-Hydroxy-7-oxo-5β-cholanic acid is an important intermediate for the preparation of obeticholic acid and also an important intermediate for the preparation of ursodeoxycholic acid. [0011] Obeticholic acid (OCA, also known as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCC07J9/00
Inventor 沈建伟刘敏
Owner SUZHOU JINGYE MEDICINE & CHEM
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