[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]=[N+:16]=[N-:17])[O:11][C:10]2=[O:18])[CH:5]=[CH:6][C:7]=1[I:8].[Cl:19][C:20](S(Cl)(=O)=O)=[CH2:21]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:21]=[C:20]([Cl:19])[N:17]=[N:16]3)[O:11][C:10]2=[O:18])[CH:5]=[CH:6][C:7]=1[I:8]A stirred mixture of (5R)-3-(3-fluoro-4-iodophenyl)-5-azidomethyl-1,3-oxazolidin-2-one (1 g, 28 mmol) and 1-chloro-1-ethenesulfonyl chloride (1 g, 6.2 mmol) was heated in a pressure tube at 80° C. for one hour. The reaction mixture was cooled to room temperature, diluted with chloroform (15 mL), and heated at 80° C. for an additional 4 hours. The reaction mixture was cooled to room temperature and the precipitate was collected by filtration and washed with little dichloromethane to yield the title compound as a colorless amorphous solid (725 mg, 62%).
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