HCID 178503205, compound → HCID 178503204, compound

Participants

Reaction Steps

cis-4-{[5-Fluoro-2-(3-methylsulfanyl-phenoxy)-pyridine-3-carbonyl]-amino}-cyclohexanecarboxylic acid benzyl ester (1.75 g, 3.54 mmol) was dissolved in a solution of 4.4% formic acid in methanol (40 ml) and this was added dropwise to a suspension of palladium black (2 g) in 4.4% formic acid in methanol (120 ml) at room temperature under nitrogen. The mixture was stirred for 2 h, then filtered through arbocel washing with methanol (5×50 ml). The filtrates were concentrated under reduced pressure and basified to pH10 with 1M sodium hydroxide solution (50 ml). The aqueous phase was extracted with diethylether (3×50 ml) then acidified to pH1 with concentrated hydrochloric acid. After extraction with diethylether (3×50 ml) the combined organic extracts were washed with water (10 ml), dried over MgSO4 and the solvent removed under reduced pressure to give cis-4-{[5-Fluoro-2-(3-methylsulfanyl-phenoxy)-pyridine-3-carbonyl]-amino}-cyclohexanecarboxylic acid (691 mg) as a white solid.

Provenance & Evidence