2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 88879943, compound

Participants

Reaction Steps

To a solution of rac-1-[(4-cyano-4-pyridin-2-ylpiperidin-1-yl)methyl]-N-[(1R,2R)-2-(methylthio)cyclohexyl]-4-oxo-4H-quinolizine-3-carboxamide (Example 16, 0.035 g, 0.067 mmol) in 2 mL of dichloromethane at 0° C. was added 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (Davis reagent, 0.019 g, 0.074 mmol). After 45 min, the mixture was washed 3× with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-5% methanol in dichloromethane to provide the title compound that gave a proton NMR spectra consistent with theory and a high resolution mass spectrum (ES+) m/z of 532.2390 calculated for M+H+ [C29H34N5O3S: 532.2377]: 1H NMR (400 MHz, CDCl3) δ 10.02-9.99 (m, 1H), 9.42-9.40 (m, 1H), 8.66 (s, 1H), 8.60-8.57 (m, 1H), 8.22-8.19 (m, 1H); 7.76-7.67 (m, 2H), 7.62-7.60, 7.32-7.21 (m, 1H), 4.29-4.26 (m, 1H), 4.13-4.03 (m, 1H), 3.81 (s, 2H), 3.01-2.83 (m, 2H), 2.82-2.78 (m, 1H), 2.61 (s, 3H), 2.47-2.43 (m, 1H), 2.32-2.26 (m, 2H), 2.14-2.06 (m, 4H), 2.05-1.84 (m, 2H), 1.83-1.36 (m, 2H).

Provenance & Evidence