Sodium Hydroxide → HCID 25007441, compound

Participants

Reaction Conditions

Reaction Steps

2M aqueous sodium hydroxide (2.050 mL, 4.10 mmol) was added in one portion to methyl 4-[4-[[5-(difluoromethoxy)-2-adamantyl]carbamoyl]-5-propylsulfanylpyrazol-1-yl]benzoate (Intermediate #95) (459 mg, 0.82 mmol) in methanol (10 mL). The resulting mixture was stirred at 20° C. for 18 hours and then a further 4 hours at 55° C. 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 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-[[5-(difluoromethoxy)-2-adamantyl]carbamoyl]-5-propylsulfanylpyrazol-1-yl]benzoic acid (284 mg, 63.5%).

Provenance & Evidence