Reaction SMILES: [NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:34]/[O:35][C:36]([C:39]([O:41]C(C)(C)C)=[O:40])([CH3:38])[CH3:37])/[C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:20]([O:22]CC4C=CC(OC)=CC=4)=[O:21])=[C:15]([CH2:18]Cl)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.C[Si](C)(C)NC(N[Si](C)(C)C)=O.[I-].[K+].C(OC([NH:67][CH2:68][C@H:69]([NH:99]/[C:100](/[NH:109]C(=O)OC(C)(C)C)=[N:101]/C(=O)OC(C)(C)C)[C:70]([NH:72][C:73]1[CH:74]=[N:75][N:76]([CH3:98])[C:77]=1[NH:78]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:71])=O)(C)(C)C.[S:117](=[O:121])(=[O:120])([OH:119])[OH:118]>CN1CCOCC1.C(OCC)(=O)C>[S:117]([O-:121])([OH:120])(=[O:119])=[O:118].[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:34]/[O:35][C:36]([C:39]([OH:41])=[O:40])([CH3:37])[CH3:38])/[C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH2:18][N+:75]4[N:76]([CH3:98])[C:77]([NH2:78])=[C:73]([NH:72][C:70](=[O:71])[C@@H:69]([NH:99][C:100]([NH2:109])=[NH:101])[CH2:68][NH2:67])[CH:74]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1
Reactant: O=S(=O)(O)O
Reactant: COc1ccc(COC(=O)C2=C(CCl)CS[C@@H]3[C@H](NC(=O)/C(=N\OC(C)(C)C(=O)OC(C)(C)C)c4nsc(N)n4)C(=O)N23)cc1
Reactant: Cn1ncc(NC(=O)[C@H](CNC(=O)OC(C)(C)C)N/C(=N/C(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)c1NC(c1ccccc1)(c1ccccc1)c1ccccc1
Agent: C[Si](C)(C)NC(=O)N[Si](C)(C)C
Agent: [I-]
Agent: [K+]
Solvent: CN1CCOCC1
Solvent: CCOC(C)=O
Product: Cn1c(N)c(NC(=O)[C@H](CN)NC(=N)N)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
Product: O=S(=O)([O-])O
Temperature: 25 °C
Reaction time: 0.5 h

Procedure:
To a solution of 4-methoxybenzyl 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-chloromethyl-3-cephem-4-carboxylate (681 mg) in N-methylmorpholine (2 ml) was added 1,3-bis(trimethylsilyl)urea (1.02 g) and the mixture was stirred at room temperature for 30 minutes. To the solution was added potassium iodide (183 mg) and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added di-tert-butyl {(Z)-[((1S)-1-{[(tert-butoxycarbonyl)amino]methyl}-2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-2-oxoethyl)amino]methylylidene}biscarbamate (939 mg) and the whole mixture was stirred at 35° C. overnight. To the resulting reaction mixture was added ethyl acetate (1.7 L) and the mixture was washed successively with water, 10% aqueous sodium thiosulfate solution, 10% aqueous sodium trifluoroacetate solution and brine, dried over magnesium sulfate and filtered. The filtrate was concentrated to about 1 L in vacuo. The concentrate was poured into diisopropyl ether and the resulting precipitate was collected by filtration and dried in vacuo. To a solution of the solid in methylene chloride (3.6 ml) were added anisole (1.2 ml) and trifluoroacetic acid (3.6 ml). The resulting solution was stirred at room temperature for 4 hours and poured into diisopropyl ether. The resulting precipitate was collected by filtration and dried in vacuo to give a crude product. The crude product was purified by preparative 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 by addition of concentrated hydrochloric acid and chromatographed on Diaion (registered trademark) HP-20 eluting with 30% aqueous 2-propanol. The eluate was concentrated to about 30 ml in vacuo and 1 equivalent of 0.1M aqueous sulfuric acid solution was added. The mixture was lyophilized to give 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-(3-amino-4-{[(2S)-3-amino-2-(guanidino)propanoyl]amino}-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylic acid hydrogensulfate (115 mg) as an amorphous solid.