Sodium Hydroxide → HCID 16065390, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3-(methylthio)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (1) (40 mg, 0.097 mmol) in CH2Cl2 (1 mL) was added MCPBA (54 mg of 70-75%, 0.23 mmol) and solution allowed to stir for 1 h. Additional MCPBA (10 mg) was added and reaction heated at 40° C. for 1 h., then allowed to cool. Next was added H2O (1 mL) and a few crystals of sodium thiosulfate, CH2Cl2 (3 mL), and 1 N NaOH (2 mL-aqueous). The layers were shaken together, separated, the organics 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 (6 mg) as a white solid. 1H NMR (300 MHz, CDCl3, 65° C.) δ 8.13 (d, J=8.5 Hz, 1H), 7.92-7.76 (m, 2H), 7.59-7.25 (m, 11H), 6.19-6.08 (m, 1H), 5.27-5.15 (m, 1H), 2.96 (s, 3H), 2.28-1.87 (m, 2H), 1.00 (t, J=7.4 Hz, 3H); HRMS m/z 445.1573, calcd 445.1586.

Provenance & Evidence