[NH2:1][C:2]1[S:3][C:4]([Cl:26])=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][C@@H:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(N(CC)CC)C.[C:34]1([C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37](Br)[O:36]1)=[O:35].O>CN(C)C=O>[C:34]1([C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]([O:19][C:18]([C:14]2[N:13]3[C:21](=[O:22])[C@@H:11]([NH:10][C:8](=[O:9])[C:7]([C:5]4[N:6]=[C:2]([NH2:1])[S:3][C:4]=4[Cl:26])=[N:23][O:24][CH3:25])[C@H:12]3[S:17][CH2:16][CH:15]=2)=[O:20])[O:36]1)=[O:35]To a solution of 7β-[2-(2-amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (209 mg) in N,N-dimethylformamide (5 ml) are added triethylamine (0.07 ml) and phthalidyl bromide (128 mg), and the mixture is stirred at room temperature for 20 minutes. The reaction mixture is poured into water and the separated precipitate is collected by filtration. The solid material is dissolved in ethyl acetate, washed with water, diluted aqueous sodium hydrogen carbonate solution, water, diluted aqueous phosphoric acid and water, dried, and evaporated. Purification of the residue by silica gel column chromatography gives 7β-[2-(2-amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid phthalidyl ester (220 mg).
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