Sodium Hydroxide → (S)-2-(6-((4'-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Participants

Reaction Steps

Methyl (S)-2-(6-((4′-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 3j (26 mg, 0.04 mmol) was dissolved in 5 mL of methanol, followed by addition of 1M aqueous sodium hydroxide solution (0.5 mL, 0.43 mmol). The reaction solution was reacted for 1.5 hours. The solution was concentrated under reduced pressure, mixed with 3 mL of water, 1M citric acid was added dropwise to adjust the pH to 4-5, and extracted with ethyl acetate (20 mL×2). The combined organic extracts were washed with saturated sodium chloride solution (30 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (S)-2-(6-((4′-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid 3 (12 mg, yield 47.4%) as a white solid.

Provenance & Evidence