Water → HCID 11027083, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 11.19 g (59.1 mmol) of (R)-N-tert-butoxycarbonylalanine in 70 mL of N,N-dimethylformamide was added 6.7 g (48.5 mmol) of K2CO3, and 6.9 mL (58.0 mmol) of benzyl bromide. The reaction was stirred at 80° C. for 40 min, then poured into 350 mL of H2O. The aqueous mixture was extracted with diethyl ether (3×50 mL), then the combined ether layers were back extracted with H2O (2×50 mL), and brine (1×50 mL), dried over MgSO4, filtered, and concentrated in vacuo to furnish the titled compound as a colorless oil. MS (ESI) m/z=280 (M+H)+, 297 (M+NH4)+, 302 (M+Na)+: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.25 (d, J=7.5 Hz, 3H) 1.37 (s, 9H) 4.06 (m, 1H) 5.07 (d, J=12.9 Hz, 1H) 5.15 (d, J=12.5 Hz, 1H) 7.34 (m, 6H).

Provenance & Evidence