Sodium Hydroxide → HCID 25007066, compound

Participants

Reaction Conditions

Reaction Steps

2M aqueous sodium hydroxide (1.671 mL, 3.34 mmol) was added in one portion to methyl 4-[4-(2-adamantylcarbamoyl)-5-cyclohexylsulfanyl-pyrazol-1-yl]benzoate (Intermediate #84) (330 mg, 0.67 mmol) in methanol (10 mL). The resulting mixture was stirred at 20° C. for 18 hours. The reaction mixture was concentrated and diluted with water (50 mL), and washed with ether (20 mL). The aqueous solution was adjusted to pH 3 with 2M HCl and extracted with EtOAc (2×25 mL), and the combined extracts washed to sequentially with water (2×20 mL) and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford 4-[4-(2-adamantylcarbamoyl)-5-cyclohexylsulfanyl-pyrazol-1-yl]benzoic acid (321 mg, 100%).

Provenance & Evidence