Sodium Hydroxide → {5-[4-(1-ethyl-1-{4-[2-(1-hydroxy-cyclohexyl)-ethyl]-3-methyl-phenyl}-propyl)-phenyl]-pyridin-3-yl}-acetic Acid

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Reaction Steps

A 2 N sodium hydroxide aqueous solution (0.12 mL, 0.23 mmol) was added to a solution of {5-[4-(1-ethyl-1-{4-[2-(1-hydroxy-cyclohexyl)-ethyl]-3-methyl-phenyl}-propyl)-phenyl]-pyridin-3-yl}-acetic acid methyl ester (Example 149-(1); 19.9 mg, 0.038 mmol) in methanol (0.4 mL), and the mixture was stirred at room temperature for two hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by thin layer silica gel chromatography (dichloromethane:methanol=9:1) to give the title compound (12.5 mg, 64%).

Provenance & Evidence