Acetic Anhydride → HCID 68771702, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-E-3-(2-phenyl-propylcarbamoyl)-acrylic acid (1.44 g, 6.2 mmol), NaOAc (305 mg, 3.7 mmol), and Ac2O (6 mL) was heated at 120° C. for 5 h. The mixture was concentrated, and the residue was stirred vigorously with satd. aq. NaHCO3. The resulting mixture was extracted with DCM (3×). The combined organic layers were dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (EtOAc/hexanes) to provide 340 mg (26%) of the desired maleimide as a white solid. 1H NMR (400 MHz, CDCl3): 7.32-7.26 (m, 2H), 7.24-7.17 (m, 3H), 6.60 (s, 2H), 3.70 (dd, J=13.7, 8.2, 1H), 3.61 (dd, J=13.7, 7.8, 1H), 3.23 (app. sextet, J=7.7, 1H), 1.26 (d, J=7.0, 3H).

Provenance & Evidence