Hydroxyamine hydrochloride → (1-[4-(4-Hydroxyimino-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of {1-[4-(2-phenyl-4-thioxo-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (33.4 mg, 0.069 mmol), hydroxylamine hydrochloride (14.4 mg, 0.207 mmol) and sodium acetate (17 mg, 0.207 mmol) in IMS (5 mL) was stirred at 80° C. for 16 hours. The cooled reaction mixture was partitioned between DCM and water. The aqueous phase was isolated and extracted with DCM. The combined organic extracts were evaporated to dryness. The resultant residue was subjected to flash chromatography (SiO2, 2% MeOH in DCM) to afford the title compound (27.2 mg, 82%) as a pale yellow solid. LCMS (Method A): RT=4.96 min, [M+H]+=483.

Provenance & Evidence