[C:1]([C@@H:4]([NH:12][S:13]([C:16]1[S:17][C:18]([Cl:21])=[CH:19][CH:20]=1)(=[O:15])=[O:14])[C@H:5]([CH3:11])[CH2:6][C:7]([F:10])([F:9])[F:8])(=[O:3])[CH3:2].[CH3:22][Mg]Br.CCOC(C)=O.CCCCCC>C1COCC1>[Cl:21][C:18]1[S:17][C:16]([S:13]([NH:12][C@H:4]([C:1]([OH:3])([CH3:22])[CH3:2])[C@H:5]([CH3:11])[CH2:6][C:7]([F:10])([F:9])[F:8])(=[O:15])=[O:14])=[CH:20][CH:19]=1A solution of N-[(1S,2R)-1-acetyl-4,4,4-trifluoro-2-methylbutyl]-5-chlorothiophene-2-sulfonamide (prepared as in Example 17, 0.100 g, 0.275 mmol) in THF (5 mL) was stirred under nitrogen at 0° C. Methyl magnesium bromide (3.0 M in ethyl ether, 0.266 mL, 0.824 mmol,) was added dropwise and the resulting solution was stirred for 19 h at 25° C. After this time period, the reaction was complete by TLC (1:2 EtOAc/hexane). The solution was quenched with saturated aqueous NH4Cl (10 mL) and extracted with ether (40 mL). The organic layer was washed with brine (20 mL) and then dried over MgSO4 to obtain a crude oil (0.110 g). The crude product was purified by the Biotage Flash™ 40 chromatography system, eluent: 1:4 EtOAc-hexanes, to afford 5-chloro-N-[(1S,2R)-4,4,4-trifluoro-1-(1-hydroxy-1-methylethyl)-2-methylbutyl]thiophene-2-sulfonamide as a white solid (0.049 g, 46.6%). Mass Spectrum (−ESI): 378 (M−H)−.
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