[F:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-])=O)=[CH:12][C:7]=2[CH2:6][S:5]1(=[O:17])=[O:16].CCOC(C)=O>[Pd]>[NH2:13][C:11]1[CH:10]=[CH:9][C:8]2[N:4]([CH2:3][CH2:2][F:1])[S:5](=[O:17])(=[O:16])[CH2:6][C:7]=2[CH:12]=1The product of Step 1 (1.25 g, 4.8 mmol) is dissolved into EtOAc (30 mL) in a Parr bottle and 10% Pd/C (100 mg) added under nitrogen. The mixture is hydrogenated on a Parr apparatus for 4 hrs at 40 psi. Filtration and evaporation of solvent gave a solid (1.1 g, 99%). Mp 119-21° C. HRMS (FAB) calcd for C9H11FN2O2S +H1 231.0603, found 231.0610.
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