Hydrogen Peroxide → HCID 13477591, compound

Participants

Reaction Conditions

Reaction Steps

4.2 ml of 30% hydrogen peroxide solution was added to a stirred solution of 1.4 g of 26A in 25 ml of acetone, at 0° C. The resulting solution was stirred at 0° C. for one hour, warmed to room temperature and the solvent was evaporated. The residue was diluted with 50 ml of cold water and 20 ml of 1N sodium bicarbonate solution and the resulting mixture was extracted with ethyl acetate. The extract was washed successively with water, 1N sodium bicarbonate solution and water, dried (MgSO4) and the solvent was evaporated. The residue was chromatographed on silica gel, first eluting with n-hexane, then with 25% ethyl acetate/n-hexane, to give, on work-up, methyl (S)-(E)-4-(benzyloxycarbonylamino)-5-fluoro-2-pentenoate (26B), as a pale yellow viscous oil.

Provenance & Evidence