Methanesulfonamide → HCID 58109469, compound

Participants

Reaction Steps

To a solution of (R)-3-((S)-1-(4-(difluoromethoxy)phenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one (0.0332 g, 0.0784 mmol) and methanesulfonamide (0.0549 g, 0.577 mmol) in dry toluene (2 mL) was added (cyanomethene)tributylphosphorane (CMBP, 0.1720 g, 0.713 mmol) at rt under N2. The mixture was stirred for 19 h at rt. After the solvents were removed in vacuo, the residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ 5 μm 19×50 mm column, 10%→90% CH3CN/H2O, 0.1% CF3COOH over 8 min and then 90% CH3CN/H2O, 0.1% CF3COOH over 2 min, flow rate 20 mL/min) to afford 0.0137 g (35%) of N-(3-((R)-3-((S)-1-(4-(difluoromethoxy)phenyl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propyl)methanesulfonamide. LC-MS Method 1 tR=1.64 min, m/z=523 (MNa+), 501 (MH+), 171; 1H NMR (400 MHz, CD3OD) δ 7.24-7.21 (m, 2H), 7.01 (t, J=8.6 Hz, 2H), 6.92 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.5 Hz, 2H), 6.65 (t, J=73.8 Hz, 1H), 5.45 (q, J=7.0 Hz, 1H), 3.04-3.00 (m, 1H), 2.93-2.86 (m, 2H), 2.77 (s, 3H), 2.38-2.34 (m, 1H), 2.22-2.09 (m, 2H), 1.92-1.82 (m, 2H), 1.58-1.50 (m, 1H), 1.44 (d, J=7.0 Hz, 3H), 1.26-1.18 (m, 1H); 19F NMR (376 MHz, CD3OD) δ −83.93 (d, J=75.0 Hz), −117.33 (m).

Provenance & Evidence