Synthesis and characterization of phenyl alanine-based C2-symmetric chiral amides

In this study, N-boc-D-phenylalanine was used as a starting material to synthesize eight different C2 symmetric amide compounds with two chiral centers. For this purpose, boc-mono-amide compounds 1a-d were obtained in high yields (at least 89%) by reacting N-Boc-D-phenylalanine with 4-phenylbutylamine, 4-butylaniline, tert-butylbenzylamine and cyclohexylamine, respectively. By removing the Boc group with TFA/AcOH, amide-amine compounds 2a-d were obtained in high yields (at least 10%). In the last step of the synthesis, a total of eight new C2-symmetric chiral tetraamide compounds, namely 3a-d and 4a-d, were synthesized by reacting compounds 2a-d with isophthaloyl chloride and diglycoyl chloride, respectively. As a result, a total of 16 amide compounds, 14 of which were new and 8 of which were tetramides, were synthesized. FTIR, 13C and 1H NMR analyzes were performed for all synthesized compounds.