Experimental and theoretical studies of the absolute configuration of (2S,1′R) and (2R,1′R)-2-acetoxymethyl-3-phenyl-N-(1′-phenylethyl)-propionamide

Two diastereoisomers (2S,1′R) and (2R,1′R)-2-acetoxymethyl-3-phenyl-N-(1′-phenylethyl)-propionamide(2), have been studied to investigate their discrimination on the absolute configuration using nuclear magnetic resonance (NMR), infrared (IR) spectroscopy were performed. The experimental results were supported by performing density functional theory (DFT) calculations for the NMR, IR spectra using the Becke 3-parameter, Lee, Yang and Parr (B3LYP) functional and the 6-311+G** basis set.