Cheah et al. have reported the synthesis of antibacterial peptidometics via ring opening of N-acetylisatins (1  ) with amino acid methyl esters (2  ), or methyl esters of di- and tri-peptides (Tetrhedron Lett. 2008  , 49, 2965-2968; Tetrahedron 2011  , 67, 7603-7610). We are modifying this methodology to develop a green, microscale experiment for the introductory organic chemistry laboratory. 1H NMR spectra of adducts 2   may exhibit diastereotopic hydrogens (e.g. 2  , R = benzyl) or diastereotopic methyls (e.g., 2 , R = isopropyl).

Green organic chemistry experiments: Glyoxylamide synthesis via ring opening of <i>N</i>-acetylisatins with amino acid methyl esters

245th National Meeting (2013)

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Green organic chemistry experiments: Glyoxylamide synthesis via ring opening of N-acetylisatins with amino acid methyl esters