Back to results
US 11,186,558 B2Granted
Synthetic methods
AssigneeGlaxosmithkline Intellectual Property (No.2) Limited
InventorsGregg Barcan, Jiasheng Guo, Christopher W. Morgan, Gheorghe D. Roiban, Peter W. Sutton
Life of this patent
Estimating the term…
Abstract
Methods for the preparation of the following compound are disclosed. The compound can be incorporated into pharmaceutical formulations, including tablets and such tablets can be used for treating cholestatic liver diseases.
Claims21
A method for synthesis of the compound GSK2330672:
- comprising the step of preparation of intermediate A, (R)-2-butyl-2-ethyloxirane
- followed by conversion of (R)-2-butyl-2-ethyloxirane through one or more steps to GSK2330672.
A method for synthesis of the compound GSK2330672:
- comprising the step of preparation of intermediate H:
- followed by conversion of intermediate H through one or more steps to GSK2330672.
A method for synthesizing the compound GSK2330672:
- comprising the steps of:
- preparing intermediate A, (R) -2 -butyl-2 -ethyloxirane
- by kinetic resolution of racemic 2-butyl-2-ethyloxirane with an epoxide hydrolase;
- reacting (R)-2-butyl-2-ethyloxirane with 3-hydroxy-4-methoxythiophenol to produce intermediate C:
- converting intermediate C via a stereoselective Ritter reaction to intermediate E:
- benzoylating intermediate E to produce intermediate F:
- cyclizing intermediate F followed by diastereoselective sulfoxidation to produce intermediate H:
- reducing the imine of intermediate H to produce intermediate I:
- and
- sulfoxidizing intermediate Ito produce intermediate J:
- followed by conversion of intermediate J through one or more steps to GSK2330672.
8 more elements
Dependencies are inferred from the claim text.