O-benzhydrylhydroxylamine → 3-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid benzhydryloxy-amide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-Benzyloxymethyl-1-(4-methoxybenzene sulfonyl)-azepane-2-carboxylic acid (19 mg, 0.044 mmoL) in 0.63 mL of dimethylformamide was added 1-Hydroxy-benzotriazole hydrate (7.1 mg, 0.0525 mmoL) and O-Benzhydryl-hydroxylamine (10.4 mg, 0.0525 mmoL). This solution was cooled to 0° C. and 1-(3-Dimethylamino propyl)-3-ethylcarbodiimide hydrochloride (10 mg, 0.0525 mmoL) was added in. The reaction was warmed to ambient temperature after 20 minutes, and the reaction was stopped after 3 hours by diluting with ethyl acetate. This solution was washed sequentially with saturated sodium bicarbonate, 0.5N HCl, and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent removed under reduced pressure. The residue was purified by column chromatography (silica: 20% to 30% ethyl acetate in hexanes) to yield 3-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid benzhydryloxy-amide; MS: (M+H)+ =615, (M+NH4)+ =632.

Provenance & Evidence