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US 7,411,088 B2Granted
Stereoselective synthesis of a 4,4-disubstituted cyclohexanepropanoic acid
AssigneesMerck & Co., Inc., Merck Sharp & Dohme Corp.
InventorsKarel Marie Joseph Brands, Sarah Elizabeth Brewer, Antony John Davies, Ulf H. Dolling, Deborah Camille Hammond, David Ross Lieberman, Jeremy Peter Scott
Life of this patent
Estimating the term…
Abstract
There is provided stereoselective route to a compound of formula I: wherein R represents H or an alkali metal, Ar1 represents 4-chlorophenyl and Ar2 represents 2,5-difluorophenyl.
Claims15
A process for the preparation of a compound of formula (1):
- wherein R represents H or an alkali metal, Ar1 represents 4-chlorophenyl and Ar2 represents 2,5-difluorophenyl;
- comprising the steps of:
- (a) stirring a mixture of a cis-sulfide of formula (2) and a trans-sulfide of formula (3):
- with 4-chlorobenzenethiol in an acidic medium in which said mixture of sulfides is partially soluble, causing preferential crystallisation of cis-sulfide of formula (2);
- (b) collecting the cis-sulfide of formula (2);
- (c) oxidising the cis-sulfide of formula (2) to the corresponding sulfone;
- and optionally
- (d) neutralising the product of step (c) with alkali.
5 more elements
The compound of formula (5):
- where Ar2 is 2,5-difluorophenyl.
The compound of formula (4):
- wherein Ar2 is 2,5-difluorophenyl.
The compound of formula (2):
- where Ar1 is 4-chlorophenyl and Ar1 is 2,5-difluorophenyl.
Dependencies are inferred from the claim text.