[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[C:12]([NH2:14])[CH:11]=[CH:10][C:9]=1[F:15])([CH3:4])([CH3:3])[CH3:2].[Cl:17]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[C:12]([NH2:14])[C:11]([Cl:17])=[CH:10][C:9]=1[F:15])([CH3:4])([CH3:2])[CH3:3]To a solution of tert-butyl(5-amino-2-fluorophenyl)carbamate (795 mg, 3.51 mmol) produced in Example D17(i) in N,N-dimethylformamide (15 mL) was added 1-chloropyrrolidine-2,5-dione (493 mg, 3.69 mmol), and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (50 mL), and the mixture was extracted with ethyl acetate (50 mL, 15 mL). The combined organic layer was washed with saturated brine (10 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→90/10), and the fractions containing the object product were concentrated under reduced pressure to give the title compound (727 mg, 79%) as a yellow solid.
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