FC(F)(F)C(O)=O.C(O[C:13]([N:15](C)[N:16]1[C:25]2[C:20](=[CH:21][C:22]([I:27])=[CH:23][C:24]=2[F:26])[C:19](=[O:28])[C:18]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:17]1)=O)(C)(C)C.C(=O)(O)[O-].[Na+].O>C(Cl)Cl>[F:26][C:24]1[CH:23]=[C:22]([I:27])[CH:21]=[C:20]2[C:25]=1[N:16]([NH:15][CH3:13])[CH:17]=[C:18]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:19]2=[O:28]
A solution of trifluroacetic acid (6.40 g) in methylene chloride (5 mL) is added dropwise over a 4 minute period to a solution of ethyl 1-((tert-butoxycarbonyl)(methyl)amino)-8-fluoro-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Preparation 34, 1.10 g) in methylene chloride (20 mL) at room temperature. After 3.5 h, the mixture is poured into a mixture of saturated sodium bicarbonate solution (125 mL) and water (50 mL), and extracted two times with ethyl acetate. The combined organic extracts are dried (Na2SO4) and concentrated at reduced pressure. The resulting gummy solid is stirred with diethyl ether at room temperature to afford 0.857 g (98%) of the title compound as a white solid.
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