N-Carbethoxyphthalimide → (S)-2-phthalimido-3-phenylpropionamide

Participants

Reaction Steps

By following the procedure of Example 19 but employing N-carbethoxyphthalimide and (S)-phenylalaninamide hydrochloride, there is obtained (S)-2-phthalimido-3-phenylpropionamide which can be recrystallized from ethanol to afford white crystals: mp 211-215° C.; 1H NMR (DMSO-d6)δ 7.92 (s, 5H, Ph), 7.72, 7.33 (2 s, 2H), 7.2-7.0 (m, 4H, Ar), 4.92 (dd, 1H, J=12, 4.5 Hz), 3.52 (dd, 1H, J=4.3, 13.9), 3.35 (dd, 1H, J=12, 13.9); 13C NMR (DMSO-d6)δ 169.6, 167.4, 137.7, 134.3, 131.2, 128.5, 128.1, 126.3, 122.9, 54.2, 33.7.

Provenance & Evidence