CN(C)/N=[C:4](\[C:24]([F:27])([F:26])[F:25])/[CH2:5][C:6]([NH:17][S@@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[F:16])[CH2:7][F:8].Cl.C([O:32]CC)C>O.O1CCOCC1>[CH3:21][C:20]([S@:18]([NH:17][C@:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[F:16])([CH2:5][C:4](=[O:32])[C:24]([F:27])([F:26])[F:25])[CH2:7][F:8])=[O:19])([CH3:23])[CH3:22]To a solution of (R)-N-((Z)-4-(2,2-dimethylhydrazono)-1,5,5,5-tetrafluoro-2-(2-fluoro-3-methylphenyl)pentan-2-yl)-2-methylpropane-2-sulfinamide (5.66 g, 13.24 mmol) in 10% water (5 mL) in dioxane (50 mL) was added hydrogen chloride, 1m in diethyl ether (26.5 ml, 26.5 mmol) and the resulting mixture was stirred at 40° C. for 1 h. The reaction was quenched with water, diluted with EtOAc and washed with water. The organic phase was dried over Na2SO4, filtered, concentrated and chromatographed on silica gel using 0-40% EtOAc/hexanes to afford a yellow oil as (R)-2-methyl-N-((S)-1,5,5,5-tetrafluoro-2-(2-fluoro-3-methylphenyl)-4-oxopentan-2-yl)propane-2-sulfinamide (3.80 g, 75% yield). MS m/z=385.9 [M+H]+. Calculated for C16H20F5NO2S: 385.11.
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