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Preparation method of 3-beta-peanut amide-7alpha, 12alpha, 5beta-cholane-24-carboxylic acid

A technology of arachidonic amide group and arachidonic acid chloride is applied in the production of bulk chemicals, steroids, organic chemistry, etc., which can solve the problems of high consumption of raw materials and reagents, increase of synthesis cost, and impact on production efficiency, and achieves reduction of raw material consumption, The effect of short preparation cycle and improved production efficiency

Active Publication Date: 2011-07-06
TOPHARMAN SHANGHAI CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of the methyl protecting group leads to an increase of the two-step reaction of the protective group and the deprotection group, which will result in increased steps, low overall yield, high consumption of raw materials and reagents, heavy environmental pollution, affecting production efficiency, and will inevitably cause Synthesis cost increased

Method used

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  • Preparation method of 3-beta-peanut amide-7alpha, 12alpha, 5beta-cholane-24-carboxylic acid
  • Preparation method of 3-beta-peanut amide-7alpha, 12alpha, 5beta-cholane-24-carboxylic acid
  • Preparation method of 3-beta-peanut amide-7alpha, 12alpha, 5beta-cholane-24-carboxylic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Example 1: Preparation of 3α-methanesulfonyloxy-7α, 12α-dihydroxy-5β-cholane-24-carboxylic acid (compound II-a)

[0028]

[0029] Dissolve 30 g (73.5 mmol) of cholic acid in 100 ml of pyridine, cool to 0°C, add 6.8 ml of methanesulfonyl chloride (88.2 mmol), and continue stirring at 0-10°C for 2 hours. Pour the reaction mixture into a mixture of 100 ml of ethyl acetate and 100 ml of water, stir, let stand, separate the organic layer, wash the water layer once with 100 ml of ethyl acetate, combine the organic phases, and wash with 50 ml of saturated brine , dried, and concentrated under reduced pressure to obtain white foamy solid II-a, which can be directly used in the next reaction.

Embodiment 2

[0030] Example 2: Preparation of 3α-methanesulfonyloxy-7α, 12α-dihydroxy-5β-cholane-24-carboxylic acid (compound II-a)

[0031] 30 g (73.5 mmol) of cholic acid was dissolved in 100 ml of pyridine and 100 ml of dichloromethane, cooled to 0°C, 6.8 ml of methanesulfonyl chloride (88.2 mmol) was added, and stirring was continued at 0-10°C for 2 hours. Pour the reaction mixture into a mixture of 100 ml of ethyl acetate and 100 ml of water, stir, let stand, separate the organic layer, wash the water layer once with 100 ml of ethyl acetate, combine the organic phases, and wash with 50 ml of saturated brine , dried, and concentrated under reduced pressure to obtain white foamy solid II-a, which can be directly used in the next reaction.

Embodiment 3

[0032] Example 3: Preparation of 3α-p-toluenesulfonyloxy-7α, 12α-dihydroxy-5β-cholane-24-carboxylic acid (compound II-b)

[0033]

[0034] Dissolve 30 g (73.5 mmol) of cholic acid in 100 ml of pyridine, cool to 0°C, add 16.8 g of p-toluenesulfonyl chloride (88.2 mmol), and continue stirring at 0-10°C for 2 hours. Pour the reaction mixture into a mixture of 100 ml of ethyl acetate and 100 ml of water, stir, let stand, separate the organic layer, wash the water layer once with 100 ml of ethyl acetate, combine the organic phases, and wash with 50 ml of saturated brine , dried, and concentrated under reduced pressure to obtain white foamy solid II-b, which was directly used in the next reaction.

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Abstract

The invention relates to a preparation method of 3-beta-peanut amide-7alpha, 12alpha, 5beta-cholane-24-carboxylic acid. The method adopts a two-step reaction route for preparation, which avoids the utilization of protecting groups, reduces reaction steps, decreases unnecessary raw material consumption, increases production efficiency, reduces environment pollution, and has the advantages of high yield and low cost.

Description

technical field [0001] The invention relates to a preparation method of cholic acid derivatives, more specifically, to a preparation method of 3-β-arachidamide-7α, 12α, 5β-cholane-24-carboxylic acid. Background technique [0002] 3-β-Arachidamide-7α, 12α, 5β-cholane-24-carboxylic acid (Aramchol) is a new type of compound used in the treatment of gallstones, which can delay the crystallization rate of cholesterol and can promote the dissolution of Cholesterol crystals formed (Gut, 2001, 48, 75-79; Lipids, 2001, 36, 1135-1140; Hepatology, 35, 597-600; WO 1999052932; WO 2009060452). In addition to treating gallstones, this compound can also be used to treat fatty liver due to poor dietary habits, reduce the possibility of arteriosclerosis, and increase the secretion of neutral stearyl alcohol (Hepatology, 38, 436-442; Pathobiology 2002, 70, 215-218; Biochem. Soc. Trans., 2004, 32, 131-133). Its structural formula is as follows: [0003] [0004] At present, the synthesis ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCC07J41/0011C07J41/0005C07J9/005C07J31/006C07J41/0027Y02P20/55
Inventor 蒋翔锐郭利军戴伊如李剑峰索瑾张容霞刘正
Owner TOPHARMAN SHANGHAI CO LTD
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