To synthesize a Ugi aduct from Benzaldehyde, Furfuryl amine, Benzylisocyanide and BOC-GLY-OH in methanol using Ugi 4Component Reaction.

BOC-GLY-OH,  STR IS

Procedure

A solution of Benzaldehyde (212 uL, 2.09 mmol) and Furfuryl amine (FFA) (235uL, 2.66 mmol )was prepared in methanol-d4 in a 4mL volumetric flask to form an imine overnight. The next day a solution of BOC-GLY-OH(350 mg, 1.99 mmol), andBenzylisocyanide (240uL, 1.97 mmol) made up in a 4ml volumetric flask in methanol was added to the preformed imine. The product was filtered and washed with ice cold methanol (5mL).
Characterization

tert-butyl 5-(benzylamino)-3-(furan-2-ylmethyl)-2,5-dioxo-4-phenylpentylcarbamate:

Colorless Crystals; M.pt 146-148C;

1HNMR ( ppm, CDCl3) 1.43 (s, 9H), 4.18 (m, 2H), 4.43 (m, 2H), 4.48 (s, 2H), 5.46 (s, 1H), 5.68 (s, 1H), 5.94 (s, 1H), 6.09 (m, 1H), 6.30 (s, 1H), 7.10-7.50 (m 11H)

13C NMR ( ppm, CDCl3) 28.3, 42.5, 42.8, 43.6, 63.0, 79.5, 107.9, 110.3, 110.8, 127.4, 127.6, 128.6, 128.7, 129.6, 134.2, 137.7, 142.0, 149.5, 155.7, 169.0, 170.3;

FAB HRMS: m/z 478.2366; calcd for C27H31N3O5 (M+H).