Sodium Hydroxide → 4-[4-(2-Adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoic acid

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Reaction Steps

Methyl 4-[4-(2-adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate (190 mg, 0.42 mmol) (Intermediate #2) was dissolved in methanol (10 mL) and treated at ambient temperature with 2M aqueous sodium hydroxide solution (1.05 mL, 2.1 mmol). The mixture was stirred at ambient temperature for 18 h. and then heated to 65° C. for a further 2 h. Methanol was removed by evaporation under reduced pressure and the clear solution diluted with water (25 ml). 2M HCl was added to pH4 and the mixture extracted with ethyl acetate (2×25 mL). The combined extracts were washed with water (2×10 mL) and brine (10 mL), dried (MgSO4) and evaporated to give the title compound as a white solid. (174 mg, 94%)

Provenance & Evidence