[Br:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH:19][S@@](C(C)(C)C)=O)([CH2:12][C@H:13]([OH:18])[C:14]([F:17])([F:16])[F:15])[CH2:10][F:11])[C:5]([F:8])=[N:6][CH:7]=1.Cl.O1CCOCC1>C(Cl)Cl.CO>[NH2:19][C@@:9]([C:4]1[C:5]([F:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH2:10][F:11])[CH2:12][C@H:13]([OH:18])[C:14]([F:16])([F:15])[F:17](R)-N-((2S,4S)-2-(5-bromo-2-fluoropyridin-3-yl)-1,5,5,5-tetrafluoro-4-hydroxypentan-2-yl)-2-methylpropane-2-sulfinamide (3.68 g, 8.12 mmol) was dissolved in 36 mL methylene chloride and 18 mL MeOH. The solution was stirred at room temperature. Hydrogen chloride, 4M in 1,4-dioxane (20.30 ml, 81 mmol) was added and the reaction mixture was stirred for 1.5 h. The reaction was concentrated, then EtOAc and water was added, followed by addition of saturated sodium bicarbonate solution for neutralization. The layers were separated and the aqueous layer was extracted with EtOAc three times. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to give crude material of (2S,4S)-4-amino-4-(5-bromo-2-fluoropyridin-3-yl)-1,1,1,5-tetrafluoropentan-2-ol that was used without further purification.
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