Benzyl Bromide → HCID 69414732, compound

Participants

Reaction Steps

2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid benzyl ester (2 g, 5 mmol) in DMF (10 mL) was added over 10 min to a slurry of NaH (240 mg 60% dispersion in mineral oil, 6 mmol) in DMF (10 mL) at 0° C. The resultant solution was stirred at this temperature for 30 min. BnBr (1.128 g, 0.785 mL, 6.5 mmol) in DMF (5 mL) was then added slowly to the solution at 0° C. and then mixture warmed to room temperature over 1.5 h. After stirring overnight the reaction was quenched and the solvent removed. The residue was taken up into EtOAc and washed with water, brine and dried with MgSO4. Filtration and removal of the solvent yielded crude material which was subject to column chromatography (silica gel, 50% EtOAc/petroleum ether, Rf 0.85) to give the ester (2.276 g, 92%). 13C NMR (CDCl3) δ 172.0, 155.2, 137.4, 136.5, 135.4, 128.7, 128.5, 128.3, 127.5, 127.4,126.9, 126.9, 126.6, 121.9, 119.4, 119.1, 109.7, 109.2, 79.7, 66.9, 54.5, 49.8, 28.3, 27.9. ISMS: 485 (M+H),

Provenance & Evidence