HCID 178503264, compound → HCID 178503263, compound

Participants

Reaction Steps

cis-4-{[2-(4-methylsulfanyl-phenoxy)-pyridine-3-carbonyl]-amino}-cyclohexanecarboxylic acid benzyl ester (4.35 g, 9.13 mmol) was dissolved in a solution of 4.4% formic acid in methanol (100 ml) and dimethylformamide (25 ml) and this was added to a suspension of palladium black (5 g) in 4.4% formic acid in methanol (300 ml) at room temperature under nitrogen. The mixture was stirred for 2.5 h, then filtered through arbocel washing with methanol (4×200 ml). The filtrates were concentrated under reduced pressure and the residue was azeotroped with toluene (2×50 ml). The residue was then diluted with water (50 ml) and basified to pH10 with 1M sodium hydroxide pellets. The aqueous phase was extracted with diethylether (2×50 ml) then acidified to pH1 with concentrated hydrochloric acid. After extraction with diethylether (5×50 ml) the combined organic extracts were washed with water (20 ml), dried over MgSO4 and the solvent removed under reduced pressure to give cis-4-{[2-(4-methylsulfanyl-phenoxy)-pyridine-3-carbonyl]-amino}-cyclohexanecarboxylic acid (2.7 g) as a white solid.

Provenance & Evidence