反应详情

温度

20 °C

2M aqueous sodium hydroxide (1.694 mL, 3.39 mmol) was added in one portion to methyl 4-[4-(2-adamantylcarbamoyl)-5-cyclopentylsulfanyl-pyrazol-1-yl]benzoate (Intermediate #90) (325 mg, 0.68 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 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-cyclopentylsulfanyl-pyrazol-1-yl]benzoic acid (307 mg, 97%).

1. concentrationThe reaction mixture was concentrated
2. additiondiluted with water (50 mL)
3. washwashed with ether (20 mL)
4. extractionextracted with EtOAc (2×25 mL)
5. washthe combined extracts washed sequentially with water (2×20 mL) and saturated brine (20 mL)
6. dry with materialThe organic layer was dried over MgSO4
7. filtrationfiltered
8. customevaporated