UGI REACTION

Bradley, J., Baig Mirza, K., Osborne, T., Wiliams, A., Owens, K. Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling. J. Vis. Exp. (21), e942, doi:10.3791/942 (2008).

tert-Butyl (2-{[2-(tert-butylamino)-2-oxo-1-phenylethyl](2-furylmethyl)amino}-2-oxoethyl)carbamate

Characterization of the Ugi product

tert-butyl (2-{[2-(tert-butylamino)-2-oxo-1-phenylethyl](furan-2-ylmethyl)amino}-2-oxoethyl)carbamate : 

white solid; m.p.(11) 202-204 C; 

1H NMR (12, spectrum) (500MHz,δppm, CDCl3) 1.33 (s, 9H), 1.45 (s, 9H), 4.21 (m, 2H), 4.49 (d, J=18Hz, 1H), 4.50 (d, J=18Hz, 1H), 5.47 (s, 1H), 5.60 (s, 1H), 5.62 (s, 1H), 5.89 (s, 1H), 6.10 (s, 1H), 7.19 (s, 1H), phenyl 7.21-7.37 (m, 5H); 

13C NMR (13, spectrum) (500MHz, δppm, CDCl3) 28.3, 28.6, 42.3, 42.8, 51.7, 62.9, 79.5, 107.7, 110.4, 128.5, 128.7, 129.6, 134.7, 141.9, 149.8, 155.7, 168.4 170.2; IR (14,spectrum) (Ʋmax cm-1 ATR): 1645,1673,1699, 3331; 

FAB-HRMS (15, spectrum) (calculated for C24H33N3O5 m/z 444.2498 [M+H], obtained 444.2517.)

Synthesis of the Ugi Adduct  using piperonal , 5-MFA (18), Boc-Gly-OH (), and t-butyl isocyanide .

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