Synthetic and NMR-Spectroscopic Investigation of Benzylamine Addition to N-Maleylamino Acid Derivatives

Article abstract of DOI:10.1007/BF00816859

During the addition of amines to maleylamino acids in general β-amino derivatives are formed.In order to change the reactivity within the vinylogous maleyl system we introduced the β-benzylester group into the starting compound N-(cis-β-carboxyacryloyl)-phenylalanine methylester 1.The obtained benzylester 2 is adding benzylamine in α-position yielding N-benzyl-α-aspartyl(β-benzyl)-phenylalanine methylester 4.The addition reaction was investigated by 1H-NMR-spectroscopy.The structures of the compounds have been confirmed by elemental analysis, IR, 1H-NMR and 13C-NMR spectroscopy.Keywords. α-Aspartyl peptides; N-Maleylamino acid derivatives; Nucleophilic addition.