SYNTHESIS OF UGI ADDUCT

Exp108-061407-2.JPG

 

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 (external image delta.gif 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 (external image delta.gif 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).

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About DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D,( ICT), Worlddrugtracker, Helping millions with chemistry sites, million hits on google
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