Sodium Hydroxide → HCID 25183508, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 122 (85.0 mg; 0.22 mmol) in tetrahydrofuran (5 mL) and methanol (5 mL) was added aqueous sodium hydroxide (7.5 mL; 2N) and then heated at 80° C. for 16 hours. The reaction mixture was allowed to cool to room temperature and then extracted with diethyl ether. The aqueous layer was separated and acidified with aqueous hydrochloric acid (15 mL; 2N) then extracted with ethyl acetate (2×15 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting crude residue was purified by automated silica gel column chromatography (Biotage®) eluting with dichloromethane/methanol to give the title product as an off-white solid (47 mg).

Provenance & Evidence