Reaction SMILES: [C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:52]/[O:53][CH3:54])/[C:27]([NH:29][C@@H:30]2[C:50](=[O:51])[N:32]3[C:33]([C:38]([O:40][CH2:41][C:42]4[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=4)=[O:39])=[C:34](O)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:74][O:75][C:76]1[CH:101]=[CH:100][C:79]([CH2:80][O:81][C:82]2[C:87]([O:88][CH2:89][C:90]3[CH:95]=[CH:94][C:93]([O:96][CH3:97])=[CH:92][CH:91]=3)=[CH:86][N:85]=[C:84]([CH2:98][OH:99])[CH:83]=2)=[CH:78][CH:77]=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1.C(OC(=O)C)C>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:52]/[O:53][CH3:54])/[C:27]([NH:29][C@@H:30]2[C:50](=[O:51])[N:32]3[C:33]([C:38]([O:40][CH2:41][C:42]4[CH:43]=[CH:44][C:45]([O:48][CH3:49])=[CH:46][CH:47]=4)=[O:39])=[CH:34][CH:35]([O:99][CH2:98][C:84]4[N:85]=[CH:86][C:87]([O:88][CH2:89][C:90]5[CH:91]=[CH:92][C:93]([O:96][CH3:97])=[CH:94][CH:95]=5)=[C:82]([O:81][CH2:80][C:79]5[CH:78]=[CH:77][C:76]([O:75][CH3:74])=[CH:101][CH:100]=5)[CH:83]=4)[S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
Reactant: CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OCc3ccc(OC)cc3)=C(O)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1
Reactant: COc1ccc(COc2cnc(CO)cc2OCc2ccc(OC)cc2)cc1
Agent: CCOC(=O)/N=N/C(=O)OCC
Agent: c1ccc(P(c2ccccc2)c2ccccc2)cc1
Solvent: CCOC(C)=O
Solvent: C1CCOC1
Product: CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OCc3ccc(OC)cc3)=CC(OCc3cc(OCc4ccc(OC)cc4)c(OCc4ccc(OC)cc4)cn3)S[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1
Reaction time: 1 h
Yield: 64.8 %

Procedure:
340 mg (0.446 mmol) of p-methoxybenzyl 7β-[2-(2-tritylaminothiazol-4-yl) -(Z)-2-methoxyiminoacetamido]-3-hydroxy-3-cephem-4-carboxylate and 146 mg (0.557 mmol) of triphenylphosphine were dissolved in 7 ml of tetrahydrofuran, and a solution of tetrahydrofuran (3.5 ml) of 170 mg (0.446 mmol) of 4,5-bis(4-methoxybenzyloxy)-2-hydroxymethylpyridine was added thereto at -20° C. under nitrogen atmosphere. Then, a solution of 0.087 ml (0.55 mmol) of diethylazodicarboxylate in 3.5 ml of tetrahydrofuran was dropwise added to the solution at -20° C., and the mixture was stirred for 1 hour at the same temperature. 30 ml of ethylacetate was added thereto. The solution was washed sequentially with water, a 1N hydrochloric acid aqueous solution, a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Wakogel C-300, elution with 1-2% methanol-chloroform) to obtain 325 mg (yield: 64.8%) of p-methoxybenzyl 7β-[2-(2-tritylaminothiazol-4-yl)-(Z) -2-methoxyiminoacetamido]-[3,4-bis(4-methoxybenzyloxy) -6-pyridylmethoxy]-3-cephem-4-carboxylate as a powder. 325 mg (0.289 mmol) of this powder was dissolved in 28 ml of methylene chloride, and a solution of 0.067 ml (0.592 mmol) of methyltrilrate in 2 ml of methylene chloride was dropwise added thereto at -20° C. under nitrogen atmosphere. The mixture was stirred for 1 hour at room temperature. The solvent was distilled off, and the residue was triturated to obtain 355 mg (yield: 95.2%) of p-methoxybenzyl 7β-[2-(2-tritylaminothiazol-4-yl) -(Z)-2-methoxyiminoacetamido]-[3,4-bis(4-methoxybenzyloxy) -1-methyl-6-pyridiniomethoxy]-3-cephem-4-carboxylate trifluoromethanesulfonate as a powder. 355 mg (0.275 mmol) of this powder was dissolved in 429 mg (2.79 mmol) of 3-methyl-4-methylthiophenol, 2 ml of methylene chloride and 0.34 ml (2.5 mmol) of thioanisole, and 2 ml of trifluoroacetic acid was added thereto under cooling with ice. The mixture was stirred for 1 hour at room temperature. The solvent was distilled off, and ethyl ether was added to the residue to obtain the trifluoroacetate of the above-identified compound as a powder. This powder was dissolved in water and insolubles were filtered off. The filtrate was purified by reversed phase column chromatography (Chemco LC-SORB, SP-β-ODS, elution with 30% methanol aqueous solution) and freeze-dried to obtain 28.1 mg (yield: 19%) of the above-identified compound.