A facile synthesis of ursodeoxycholic acid and obeticholic acid from cholic acid

Xiao Long He; Li Ting Wang; Xiang Zhong Gu; Jie Xin Xiao; Wen Wei Qiu

doi:10.1016/j.steroids.2018.10.009

A facile synthesis of ursodeoxycholic acid and obeticholic acid from cholic acid

Xiao Long He, Li Ting Wang, Xiang Zhong Gu, Jie Xin Xiao, Wen Wei Qiu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

A novel synthetic route of producing ursodeoxycholic acid (UDCA) and obeticholic acid (OCA) was developed through multiple reactions from cheap and readily-available cholic acid. The reaction conditions of the key elimination reaction of mesylate ester group were also investigated and optimized, including solvent, base and reaction temperature. In the straightforward synthetic route for preparation of UDCA and OCA, most of the reaction steps have high conversions with average yields of 94% and 92%, and overall yield up to 65% (7 steps) and 36% (11 steps) from cholic acid, respectively. This promising route offers economical and efficient strategies for potential large-scale production of UDCA and OCA.

Original language	English
Pages (from-to)	173-178
Number of pages	6
Journal	Steroids
Volume	140
DOIs	https://doi.org/10.1016/j.steroids.2018.10.009
State	Published - Dec 2018

Keywords

Cholic acid
Obeticholic acid
Synthesis
Ursodeoxycholic acid

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10.1016/j.steroids.2018.10.009

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title = "A facile synthesis of ursodeoxycholic acid and obeticholic acid from cholic acid",

abstract = "A novel synthetic route of producing ursodeoxycholic acid (UDCA) and obeticholic acid (OCA) was developed through multiple reactions from cheap and readily-available cholic acid. The reaction conditions of the key elimination reaction of mesylate ester group were also investigated and optimized, including solvent, base and reaction temperature. In the straightforward synthetic route for preparation of UDCA and OCA, most of the reaction steps have high conversions with average yields of 94\% and 92\%, and overall yield up to 65\% (7 steps) and 36\% (11 steps) from cholic acid, respectively. This promising route offers economical and efficient strategies for potential large-scale production of UDCA and OCA.",

keywords = "Cholic acid, Obeticholic acid, Synthesis, Ursodeoxycholic acid",

author = "He, \{Xiao Long\} and Wang, \{Li Ting\} and Gu, \{Xiang Zhong\} and Xiao, \{Jie Xin\} and Qiu, \{Wen Wei\}",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Inc.",

year = "2018",

month = dec,

doi = "10.1016/j.steroids.2018.10.009",

language = "英语",

volume = "140",

pages = "173--178",

journal = "Steroids",

issn = "0039-128X",

publisher = "Elsevier Inc.",

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TY - JOUR

T1 - A facile synthesis of ursodeoxycholic acid and obeticholic acid from cholic acid

AU - He, Xiao Long

AU - Wang, Li Ting

AU - Gu, Xiang Zhong

AU - Xiao, Jie Xin

AU - Qiu, Wen Wei

PY - 2018/12

Y1 - 2018/12

N2 - A novel synthetic route of producing ursodeoxycholic acid (UDCA) and obeticholic acid (OCA) was developed through multiple reactions from cheap and readily-available cholic acid. The reaction conditions of the key elimination reaction of mesylate ester group were also investigated and optimized, including solvent, base and reaction temperature. In the straightforward synthetic route for preparation of UDCA and OCA, most of the reaction steps have high conversions with average yields of 94% and 92%, and overall yield up to 65% (7 steps) and 36% (11 steps) from cholic acid, respectively. This promising route offers economical and efficient strategies for potential large-scale production of UDCA and OCA.

AB - A novel synthetic route of producing ursodeoxycholic acid (UDCA) and obeticholic acid (OCA) was developed through multiple reactions from cheap and readily-available cholic acid. The reaction conditions of the key elimination reaction of mesylate ester group were also investigated and optimized, including solvent, base and reaction temperature. In the straightforward synthetic route for preparation of UDCA and OCA, most of the reaction steps have high conversions with average yields of 94% and 92%, and overall yield up to 65% (7 steps) and 36% (11 steps) from cholic acid, respectively. This promising route offers economical and efficient strategies for potential large-scale production of UDCA and OCA.

KW - Cholic acid

KW - Obeticholic acid

KW - Synthesis

KW - Ursodeoxycholic acid

UR - https://www.scopus.com/pages/publications/85055910251

U2 - 10.1016/j.steroids.2018.10.009

DO - 10.1016/j.steroids.2018.10.009

M3 - 文章

C2 - 30389306

AN - SCOPUS:85055910251

SN - 0039-128X

VL - 140

SP - 173

EP - 178

JO - Steroids

JF - Steroids

ER -

A facile synthesis of ursodeoxycholic acid and obeticholic acid from cholic acid

Abstract

Keywords

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