Benzyl succinimido carbonate → Methyl N-[(benzyloxy)carbonyl]-N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate

Participants

Reaction Steps

To a stirred solution of methyl N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate (2.5 g, −8.9 mmol) in dichloromethane (50 mL) was added Cbz-OSu (2.25 g, 9.0 mmol). The resulting mixture was stirred at room temperature for 3 days. The solvent was removed on a rotavap, and the crude product was purified by flash chromatography on a Biotage® system (silica, 25-80% ethyl acetate in hexanes) to yield methyl N-[(benzyloxy)carbonyl]-N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate as colorless viscous oil. MS (M+1−Boc): 309.4

Provenance & Evidence