Carbon dioxide methanol → HCID 90088627, compound

Participants

Reaction Steps

Racemic benzyl (5-(3-fluorophenyl)-9-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)carbamate (5.9 g, 14.3 mmol) was resolved under the Chiral SFC conditions. Berger SFC MGIII, Column: CHIRALPAK® IC 25×3 cm ID, 5 μm, Mobile Phase: 45/55 CO2/MeOH; Flow rate: 160 mL/min; Detector wavelength: 220 nM. The desired stereoisomer was collected as the second peak in the elution order. After evaporation of solvent, (S)-benzyl (5-(3-fluorophenyl)-9-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)carbamate (2.73 g, 46% yield) was obtained as a white solid. HPLC: RT=3.075 min Purity=99%. (H2O/MeOH with TFA, CHROMOLITH® ODS S5 4.6×50 mm, gradient=4 min, wavelength=220 nm). Chiral HPLC RT: 8.661 min(AD, 60% (EtOH/MeOH)/heptane)>99% ee. (on AD chiral column desired is the first peak, which is the second peak on the IC SFC).

Provenance & Evidence