Methanol → 3-(ethylsulfinyl)-2-phenyl-N-((S)-1-phenylpropyl)quinoline-4-carboxamide

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To a solution of 3-(ethylthio)-2-phenyl-N-[(1S)-1-phenylpropyl]quinolin-4-carboxamide (5) (300 mg, 0.70 mmol) in MeOH (25 mL) was added a solution of NaIO4 (300 mg, 1.4 mmol) in water (15 mL) while it was cooled to 0° C. The cooling bath was removed, and reaction allowed stir for 12 h. LCMS indicated no reaction take place. Added another 2 eq of NaIO4 and the reaction mixture was heated to reflux for 8 h. It was then diluted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10-35% EtOAc/CH2Cl2) to give the desired product (two diastereomers) as a solid (88 mg, 28.4%). 1H NMR (300 MHz, CDCl3) δ 0.97 (t, 3H), 1.21 (t, 3H), 2.01 (m, 2H), 2.71 (m, 2H), 5.21 (q, 1H), 7.21 (d, 2H), 7.34 (d, 2H), 7.39 (m, 2H), 7.78 (m, 2H), 7.84 (m, 2H), 8.00 (m, 1H), 8.11 (m, 2H), 8.14 (m, 1H), 8.16 (m, 1H). MS APCI, m/z=443 (M+1). LCMS: 2.15 min.

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