[H-].[Na+].[NH2:3][S:4]([CH2:7][CH2:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[F:23])[C:10](OC)=[O:11])(=[O:6])=[O:5].CO>CCCCCC.O1CCCC1>[F:23][C:15]1[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=1[CH:9]1[CH2:8][CH2:7][S:4](=[O:6])(=[O:5])[NH:3][C:10]1=[O:11]A 60% sodium hydride oil dispersion (520 mg, 13.0 mmol) is washed with hexane (3×5 ml) then dry tetrahydrofuran (30 ml) added. To this stirred ice cooled mixture is added a solution of methyl .alpha.-[2-(aminosulfonyl)ethyl]-2-fluoro-4-nitrobenzeneacetate (3.20 g, 10.0 mmol) in dry tetrahydrofuran (30 ml). After stirring for 3 hr, additional sodium hydride (300 mg, 7.5 mmol) is added. Methanol (5 ml) is added after an additional 20 hr and the reaction evaporated to dryness. The residue is partitioned between 5% methanol-chloroform (150 ml) and 1N.HCl (50 ml), and the brown solid filtered. This solid is chromatographed over silica gel (150 g) eluting with 50% acetone-hexane. Recrystallization from acetone-hexane gives the title compound as solid. mp 218-219°.
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