[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7](/[C:9](=[N:13]/[O:14][C:15](=[O:17])[CH3:16])/[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2].[Cl:18]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[Cl:18][C:6]1[S:5][C:4]([NH:3][CH:1]=[O:2])=[N:8][C:7]=1/[C:9](=[N:13]/[O:14][C:15](=[O:17])[CH3:16])/[C:10]([OH:12])=[O:11]To a suspension of 2-(2-formylaminothiazol-4-yl)-2-(Z)-(acetoxyimino)acetic acid (5 g) in tetrahydrofuran (50 ml) was added N-chlorosuccinimide (3.89 g) at room temperature. After the mixture was stirred at room temperature for 5 hours 28 minutes, the reaction mixture was poured into a mixture of 5% aqueous sodium thiosulfate solution (25 ml) and ethyl acetate (50 ml) under ice-cooling. The mixture was adjusted to pH 3.0 with 30% aqueous potassium carbonate solution under ice-cooling, stirred for 1 hour at the same temperature, and the resulting precipitate was collected by filtration to give 2-(5-chloro-2-formylaminothiazol-4-yl)-2-(Z)-(acetoxyimino)-acetic acid (4.02 g).
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