Benzophenone imine → N-(Diphenylmethylene)glycine tert-butyl ester

Participants

Reaction Steps

A solution of benzophenone imine (106.2 g; 587 mmol) and tert-butyl 2-aminoacetate hydrochloride (98.3 g; 587 mmol) in dichloromethane (1 L; HPLC grade) was stirred at ambient temperature for 20 hours. The reaction mixture was partitioned between dichloromethane (0.5 L) and water (1.5 L) and the layers were separated. The aqueous phase was extracted with dichloromethane (0.5 L) and the combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to give a slightly off-white solid. The resulting solid was triturated with n-hexane to give 141 g (83.1%) of the title product as a white solid. 1H-NMR (CDCl3, 400 MHz) δ 7.62 (d, 2H, ArH), 7.21-7.42 (m, 6H, ArH), 7.13 (d, 2H, ArH), 4.05 (s, 2H, CH2), 1.41 (s, 9H, C(CH3)3); 13C-NMR (CDCl3, 100 MHz) δ 171.5, 169.8, 139.4, 136.2, 130.4, 128.8, 128.7, 128.6, 128.0, 127.7, 81.4, 56.3, 28.1.

Provenance & Evidence