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

Steroids. 2018 Dec:140:173-178. doi: 10.1016/j.steroids.2018.10.009. Epub 2018 Oct 31.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic
  • Chenodeoxycholic Acid / analogs & derivatives*
  • Chenodeoxycholic Acid / chemical synthesis
  • Chenodeoxycholic Acid / chemistry
  • Cholic Acid / chemistry*
  • Cost-Benefit Analysis
  • Ursodeoxycholic Acid / chemical synthesis*
  • Ursodeoxycholic Acid / chemistry

Substances

  • obeticholic acid
  • Chenodeoxycholic Acid
  • Ursodeoxycholic Acid
  • Cholic Acid