Hydrochloric Acid → Methyl 3-(S)-(N-(4-methoxybenzyl)-N-(benzyloxycarbonyl)-amino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylate

Participants

Reaction Steps

To a solution of 3.1 g of methyl 3-(S)-(4-methoxybenzyl-amino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylate, prepared as in Example 61, in 50 mL of methylene chloride was added 1.36 mL of benzyl chloroformate and after 5 min 3.0 mL of DIPEA. After stirring at room temperature for 16 h, the reaction was poured into water containing 3 mL of 2N HCl and was extracted twice with methylene chloride. The organic layers were washed with a portion of brine, combined, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography eluting with 10% ethyl acetate in hexanes to obtain 3.95 g of title compound as an oil. T.l.c. (10% ethyl acetate in hexanes) Rf =0.35

Provenance & Evidence