1,2-Dichloroethane → HCID 53737479, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(tert-butoxycarbonyl)glycine (20.00 g, 114.16 mmol) in DMF (75 mL) was added benzylamine (24.9 mL, 228.32 mmol). The solution was cooled to 0° C. and treated with EDC (43.77 g, 228.32 mmol) and HOAT (15.54 g, 114.16 mmol). The reaction was stirred at 0° C. for 10 min and at rt for 2 h. The solvent was removed in vacuo, and the resulting residue was partitioned between EtOAc, ice water, and saturated aqueous NaHCO3 solution. The layers were separated, and the organic extract was washed twice with water, once with 10% aqueous KHSO4 solution, twice more with water, and once with brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford the product as a white solid 1H NMR (400 MHz, CDCl3) δ 7.35-7.26 (m, 5H), 6.44 (br s, 1H), 5.14 (br s, 1H), 4.46 (d, J=6.0 Hz, 2H), 3.83 (d, J=6.0 Hz, 2H), 1.43 (s, 9H); ES MS (M+23)=287.

Provenance & Evidence