Hydroxyamine hydrochloride → tert-butyl 1-(2-hydroxy-2-(4-(N'-hydroxycarbamimidoyl)phenyl)ethyl)azetidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of tert-butyl 1-(2-(4-cyanophenyl)-2-hydroxyethyl)azetidine-3-carboxylate (100 mg, 0.331 mmol) and sodium bicarbonate (111 mg, 1.323 mmol) in 2-propanol was added hydroxylamine hydrochloride (22.98 mg, 0.331 mmol). The reaction mixture was heated at 85° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with H2O. The organic layer was dried with MgSO4, filtered, and concentrated to yield 110 mg of tert-butyl 1-(2-hydroxy-2-(4-(N′-hydroxycarbamimidoyl)phenyl)ethyl)azetidine-3-carboxylate. MS (m+1)=336. HPLC Peak RT=0.91 minutes (Analytical Method B).

Provenance & Evidence