Trifluoroacetic acid → 3-Acetoxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid

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Reaction Steps

To a solution of 3-Acetoxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester (266 mg, 0.6 mmoL) in 1.5 mL dichloromethane at 0° C. was added 1.5 mL of trifluoroacetic acid. The reaction was gradually allowed to warm to ambient temperature, and the solvent was removed under reduced pressure after 1.4 hours. The residue was azeotroped twice with toluene and purified by column chromatography (silica: 30% ethyl acetate in hexanes with 1% acetic acid to 4% methanol in dichloromethane with 1% acetic acid) to yield 3-Acetoxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid quantitatively; MS: (M+H)+ =386, (M+NH4)+ =403.

Provenance & Evidence