[F:1][C:2]1[CH:3]=[C:4]([NH:14]C(=O)OCC(C)C)[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1.[OH-].[K+]>C(O)CO.O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH2:14])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:9][CH2:10][S:11][CH2:12][CH2:13]1A mixture of 2-methylpropyl [3-fluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]carbamate (Step 1, 2.12 g, 6.81 mmol) in ethylene glycol (25 mL) was treated with aqueous potassium hydroxide (45%, 25.5 g, 204 mmol) with vigorous stirring, and the mixture was heated to 95° C. and stirred at this temperature for 18 hrs. The reaction was then cooled to ambient temperature and diluted with water (50 mL) and CH2Cl2 (100 mL), the layers were separated, and the organic phase was washed with water (50 mL) and saline (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was chromatographed on a Flash 40M 90 g silica gel cartridge with a gradient of EtOAc/heptane (15/85-25/75), and those fractions with an Rf=0.32 by TLC (EtOAc/hexanes, 25/75) were pooled and concentrated to give the title compound, mp 96-98° C.; MS (ESI+) for C11H14NFS m/z 212 (M+H)+.
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