Water → HCID 16064397, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3-[(methylthio)methyl]-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (9) (800 mg, 1.87 mmol) at 0° C. was added MCPBA (900 mg, 70-75%, 4.31 mmol), the cooling bath removed, and reaction allowed to stir for 1 h. Additional MCPBA (100 mg) was added and reaction heated briefly to 40° C., then allowed to cool. Sodium thiosulfate (Na2S2O3.5H2O-1.5 g) and H2O (10 mL) were added and suspension stirred vigorously for 10 min., diluted with CH2Cl2, washed with aqueous 0.3 N NaOH, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-25% EtOAc/CH2Cl2) to give the desired product (630 mg, 73% yield) as a solid. 1HNMR (300 MHz, CDCl3, 52° C.) δ 8.12 (d, J=8.4 Hz, 1H), 7.83-7.68 (m, 2H), 7.61 (d, J=7.7 Hz, 2H), 7.56-7.26 (m, 10H), 5.22 (q, J=7.6 Hz, 1H), 4.74 (d, J=12.3 Hz, 2H), 2.31 (s, 3H), 2.20-1.88 (m, 2H), 1.00 (t, J=7.4 Hz, 3H); LCMS: m/z 459 (MH+).

Provenance & Evidence