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Application of silane and synthesis of tauroursodeoxycholic acid under catalysis of silane

A technology of tauroursodeoxycholic acid and ursodeoxycholic acid is applied in the directions of steroids, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc. Environmental protection and other issues, to achieve the effect of low cost, strong tolerance, and simplified synthesis process

Inactive Publication Date: 2021-04-02
CHONGQING KINBEAR BIOTECHNOLOGY CO LTD
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention intends to provide the application of a silane and the synthesis of tauroursodeoxycholic acid under its catalysis, so as to solve the problems of high cost and non-environmental protection of the existing tauroursodeoxycholic acid synthesis method

Method used

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  • Application of silane and synthesis of tauroursodeoxycholic acid under catalysis of silane
  • Application of silane and synthesis of tauroursodeoxycholic acid under catalysis of silane
  • Application of silane and synthesis of tauroursodeoxycholic acid under catalysis of silane

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Embodiment 1

[0026] The structural formulas of ursodeoxycholic acid (cas: 128-13-2) and taurine (cas: 07-35-7) are respectively shown in formula (I) - formula (II), and the molecular formula of hydrosilane is HSi(OCH (CF 3 ) 2 ) 3 , the molecular formula of aminosilane is PMBNHSi(OCH(CF 3 ) 2 ) 3 , the synthesis process of tauroursodeoxycholic acid is shown in formula (Ⅲ).

[0027]

[0028]

[0029] The synthetic method of tauroursodeoxycholic acid under silane catalysis is specifically as follows:

[0030] Synthesis steps of tauroursodeoxycholic acid: 1 mol of ursodeoxycholic acid is dissolved in tetrahydrofuran, wherein the amount of tetrahydrofuran (mL) is 4 times the mass (g) of ursodeoxycholic acid, and the unit is mL. Then, add 1 mol of hydrosilane and 0.03 mol of aminosilane, and finally add 1 mol of taurine, keep stirring at 25°C for 6 hours, and the stirring speed is 180 rpm, and finally obtain system I.

[0031] Purification steps of tauroursodeoxycholic acid: filter...

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Abstract

The invention relates to the field of synthesis of tauroursodeoxycholic acid, and discloses application of silane and synthesis of tauroursodeoxycholic acid under catalysis of the silane. The synthesis method of tauroursodeoxycholic acid under catalysis of the silane comprises the following steps: synthesis of tauroursodeoxycholic acid: under the action of hydrosilane and aminosilane, taurine andursodeoxycholic acid react to obtain a system I containing tauroursodeoxycholic acid in tetrahydrofuran. According to the application, hydrosilane firstly reacts with carboxyl of ursodeoxycholic acidin situ to obtain silicon-based carboxylate, amino silane is beneficial to conversion of silicon-based carboxylate, silicon-based carboxylate quickly reacts with taurine to obtain tauroursodeoxycholicacid, one-pot direct synthesis of tauroursodeoxycholic acid is realized, the synthesis process is simplified, the reaction conditions are mild, and the operation is simple; the method is low in cost,economical, environment-friendly and suitable for industrial production.

Description

technical field [0001] The invention relates to the field of tauroursodeoxycholic acid synthesis, in particular to the application of a silane and the synthesis of tauroursodeoxycholic acid under its catalysis. Background technique [0002] Tauroursodeoxycholic acid is the active ingredient of bear bile, referred to as TUDCA, and its chemical name is 3α, 7β-dihydroxy-cholanoyl-N-taurine. Clinically, it is mainly used in the treatment of gallbladder cholesterol stones, primary sclerosing cholangitis, primary biliary cirrhosis and chronic hepatitis C virus, etc., so it has attracted the attention of the majority of synthetic workers. Tauroursodeoxycholic acid is a combined bile acid formed by shrinking between the carboxyl group of ursodeoxycholic acid and the amino group of taurine. At present, the chemical synthesis methods are mainly divided into three categories: mixed anhydride-phenol ester method, condensation Mixture method, active thioester method. The mixed acid anh...

Claims

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Application Information

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IPC IPC(8): B01J31/02C07J41/00
CPCB01J31/0274B01J31/0275C07J41/0066
Inventor 赵志斌王伯初王丹丹程雷丁峰曹海兵曹林丹
Owner CHONGQING KINBEAR BIOTECHNOLOGY CO LTD
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