4-phenyl-2,3-dihydro-1H-imidazol-2-one → (4S)-5,5-dimethyl-3-(4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)phenyl)-4-phenyl-1,3-oxazolidin-2-one

Participants

Reaction Steps

The title compound was prepared as described in General Scheme B using intermediate C in place of intermediate B and 4-phenyl-1H-imidazol-2(3H)-one (commercially available from Sigma-Aldrich, Milwaukee, Wis.). Purification was performed using preparative LC/MS with 0.1% NH4OH in ACN and water as the mobile phase. The pure fractions were dried under reduced pressure to afford (4S)-5,5-dimethyl-3-(4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)phenyl)-4-phenyl-1,3-oxazolidin-2-one as a white solid (15 mg, 0.055 mmol, 9% yield). 1H NMR (400 MHz, DMSO-d6) δ=11.01 (br. s., 1H), 7.71-7.65 (m, 2H), 7.62-7.50 (m, 4H), 7.41-7.34 (m, 4H), 7.34-7.20 (m, 4H), 5.49 (s, 1H), 1.65 (s, 3H), 0.92 (s, 3H). m/z (ESI) 426.2 (M+H)+.

Provenance & Evidence