[NH2:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][S:10][C:11]3[N:15]=[C:14]([OH:16])[NH:13][N:12]=3)[CH2:7][S:8][C@H:3]12.[F:22][C:23]([S:26][CH2:27][C:28](Cl)=[O:29])([F:25])[F:24].[OH-].[Na+]>CC(C)=O.C([O-])(O)=O.[Na+]>[F:22][C:23]([S:26][CH2:27][C:28]([NH:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][S:10][C:11]3[N:15]=[C:14]([OH:16])[NH:13][N:12]=3)[CH2:7][S:8][C@H:3]12)=[O:29])([F:25])[F:24]To a cold solution (-20°) of 7-amino-3-(5-hydroxy-1,2,4-triazol-3-ylthiomethyl)-3-cephem-4-carboxylic acid (3.39 g., 0.01 mole) in a mixture of acetone (62.5 ml.) and 3% NaHCO3 (62.5 ml.) is added dropwise over a 30 minute period a solution of trifluoromethylmercaptoacetyl chloride (2.24 g., 0.012 mol.) in acetone (20 ml.) The solution is maintained at pH 8 by adding 10% sodium hydroxide as needed. The reaction is stirred for 20 minutes at -15° to -20° and then allowed to warm to room temperature. The solution is washed with ether, covered with ethyl acetate and acidified to pH 2. The aqueous phase is separated and extracted with ethyl acetate. The combined ethyl acetate phases are combined, washed with water, dried, and evaporated to give the title compound.
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