Reaction SMILES: C(OC([NH:8][C:9]1[S:13][N:12]=[C:11](/[C:14](=[N:45]/[O:46][C:47]([C:50]([O:52]C(C)(C)C)=[O:51])([CH3:49])[CH3:48])/[C:15]([NH:17][C@@H:18]2[C:43](=[O:44])[N:20]3[C:21]([C:27]([O:29]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:28])=[C:22]([CH2:25]Cl)[CH2:23][S:24][C@H:19]23)=[O:16])[N:10]=1)=O)(C)(C)C.[I-].[Na+].[NH2:59][C:60]1[N:64]([CH3:65])[N:63]=[CH:62][C:61]=1[NH:66][C:67]([NH:69][CH2:70][CH2:71][NH:72]C(OC(C)(C)C)=O)=[O:68].C(OCC)(=O)C>CN(C)C=O.O>[NH2:8][C:9]1[S:13][N:12]=[C:11](/[C:14](=[N:45]/[O:46][C:47]([C:50]([OH:52])=[O:51])([CH3:48])[CH3:49])/[C:15]([NH:17][C@@H:18]2[C:43](=[O:44])[N:20]3[C:21]([C:27]([O-:29])=[O:28])=[C:22]([CH2:25][N+:63]4[N:64]([CH3:65])[C:60]([NH2:59])=[C:61]([NH:66][C:67]([NH:69][CH2:70][CH2:71][NH2:72])=[O:68])[CH:62]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:10]=1
Reactant: CC(C)(C)OC(=O)Nc1nc(/C(=N/OC(C)(C)C(=O)OC(C)(C)C)C(=O)N[C@@H]2C(=O)N3C(C(=O)OC(c4ccccc4)c4ccccc4)=C(CCl)CS[C@H]23)ns1
Reactant: Cn1ncc(NC(=O)NCCNC(=O)OC(C)(C)C)c1N
Agent: [I-]
Agent: [Na+]
Solvent: CCOC(C)=O
Solvent: CN(C)C=O
Solvent: O
Product: Cn1c(N)c(NC(=O)NCCN)c[n+]1CC1=C(C(=O)[O-])N2C(=O)[C@@H](NC(=O)/C(=N\OC(C)(C)C(=O)O)c3nsc(N)n3)[C@H]2SC1
Temperature: 25 °C
Reaction time: 0.5 h
Yield: 5.2 %

Procedure:
To a solution of benzhydryl 7β-[(Z)-2-(5-tert-butoxycarbonylamino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-chloromethyl-3-cephem-4-carboxylate (500 mg) in N,N-dimethylformamide (1.0 ml) was added sodium iodide (100 mg), and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added a solution of 5-amino-4-(3-{2-[(tert-butoxycarbonyl)amino]ethyl}ureido)-1-methylpyrazole (216 mg) in N,N-dimethylformamide (1.0 ml). The whole mixture was stirred at 32° C. for 4 hours. To the resulting reaction mixture were added ethyl acetate (50 ml) and water (50 ml). The aqueous layer was separated, and the organic layer was washed with 10% aqueous sodium trifluoroacetate solution and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to about 5 ml in vacuo. The concentrate was poured into diisopropyl ether (75 ml), and the resulting precipitate was collected by filtration and dried in vacuo. To a solution of the resulting solid in methylene chloride (1.8 ml) were added anisole (0.6 ml) and trifluoroacetic acid (1.2 ml). The resulting solution was stirred at room temperature for 4 hours and poured into diisopropyl ether (80 ml). The resulting precipitate was collected by filtration and dried in vacuo to give a crude product (380 mg), which was purified by preparative high-performance liquid chromatography (HPLC) utilizing ODS column. The eluate containing a desired product was concentrated to about 30 ml in vacuo. The concentrate was adjusted to about pH 3 with concentrated hydrochloric acid and chromatographed on Diaion® HP-20 (Mitsubishi Chemical Corporation) eluting with 30% aqueous 2-propanol. The eluate was concentrated to about 30 ml in vacuo and lyophilized to give 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-{3-amino-4-[3-(2-aminoethyl)ureido]-2-methyl-1-pyrazolio}methyl-3-cephem-4-carboxylate (21 mg) as an amorphous solid.