Hydroxyamine hydrochloride → E-3-[3'-(1-adamantyl)-4'-hydroxy-biphenyl-4-yl]-N-hydroxy-acrylamide

Participants

Reaction Steps

To a solution of E-4-(3-(1-adamantyl)-4-hydroxyphenyl)cinnamic acid (2 g, 5.34 mmol) in 80 ml of DMF were added hydroxybenzotriazole hydrate (866 mg, 5.34 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (1130 mg, 6.94 mmol). The mixture was stirred at room temperature for 4 h. After addition of hydroxylamine hydrochloride (1856 mg, 26.7 mmol), followed by 3.7 ml (26.7 mmol) of TEA, the mixture was stirred at room temperature overnight. DMF was removed under reduced pressure and the residue was washed with water to obtain 5 g of a crude product. Purification by flash chromatography on silica gel (phosphate buffered) using as eluent dichloromethane/methanol 95:5 afforded 950 mg of the title compound as a white solid.

Provenance & Evidence