3,7-di(t-butyldimethylsiloxy)-6-ene-5beta-cholan-24-oic acid methyl ester

A technology of tert-butyldimethylsilyloxy and acid methyl ester, which is applied in the field of medicine and can solve problems such as inconvenient use, unstable properties of trimethylsilyl ether groups, and influence on the yield and purity of the final product.

Inactive Publication Date: 2017-02-15
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0027] Both the literature process route 2 and the literature process route 3 use 3α, 7-bis(trimethylsilyloxy)-6-ene-5β-cholane-24-acid methyl ester as a key intermediate, and these two methods exist The following questions: (1) 3α,7-bis(trimethylsilyloxy)-6-en-5β-cholan-24-oic acid methyl ester (compound 7) contains two trimethylsilyl ether groups, The trimethylsilyl ether group is unstable in nature and is sensitive to acid or alkali, making 3α, 7-bis(trimethylsilyloxy)-6-ene-5β-cholane-24-acid methyl ester I

Method used

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  • 3,7-di(t-butyldimethylsiloxy)-6-ene-5beta-cholan-24-oic acid methyl ester

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[0106] The embodiments of the present invention will be described in detail below with reference to the accompanying drawings and examples, but those skilled in the art will understand that the following drawings and examples are only used to illustrate the present invention, and should not be regarded as limiting the scope of the present invention. If specific conditions are not indicated in the drawings and embodiments, the routine conditions or the conditions recommended by the manufacturer shall be used. The reagents or instruments used without the manufacturer's indication are all conventional products that are commercially available. All anhydrous solvents used are commercially available.

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Abstract

The invention belongs to the technical field of medicines, relates to a method of preparing obeticholic acid through adopting 3,7-di(t-butyldimethylsiloxy)-6-ene-5beta-cholan-24-oic acid methyl ester as an intermediate, and particularly relates to the 3,7-di(t-butyldimethylsiloxy)-6-ene-5beta-cholan-24-oic acid methyl ester that is a chemical compound, a method of preparing the compound, and a use of the compound for preparation of the obeticholic acid. The invention also relates to a method of preparing the obeticholic acid. The method of preparing the obeticholic acid includes (1) preparing the 3,7-di(t-butyldimethylsiloxy)-6-ene-5beta-cholan-24-oic acid methyl ester and (2) preparing the obeticholic acid through adopting the 3,7-di(t-butyldimethylsiloxy)-6-ene-5beta-cholan-24-oic acid methyl ester as the intermediate.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to the compound 3,7-bis(tert-butyldimethylsilyloxy)-6-en-5β-cholan-24-acid methyl ester, the method for preparing the compound and the compound Said compound is used for the purposes of preparing obeticholic acid. The present invention also relates to a method for preparing obeticholic acid, the method comprising the following steps: step (1): preparing 3,7-bis(tert-butyldimethylsilyloxy)-6-ene-5β - cholane-24-oic acid methyl ester; and step (2): using 3,7-bis(tert-butyldimethylsilyloxy)-6-en-5β-cholan-24-oic acid methyl ester as Intermediate, preparation of obeticholic acid. Background technique [0002] Farnesoid X receptor (FXR) belongs to the family of ligand-activated transcription factor nuclear receptors, and its natural ligands include primary bile acid chenodeoxycholic acid, secondary bile acid lithocholic acid and deoxycholic acid, etc. FXR is a bile sensor, and its func...

Claims

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Application Information

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IPC IPC(8): C07J9/00
CPCC07J9/005
Inventor 李松李行舟钟武郑志兵肖军海周辛波谢云德王晓奎谢菲
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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