Reaction SMILES: [C:1]1([C:7]([NH:20][C:21]2[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH:32]([C:51]([O:53][CH:54]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[O:52])[C:33]3[CH:38]=[C:37]([O:39][C:40](=[O:42])[CH3:41])[C:36]([O:43][C:44](=[O:46])[CH3:45])=[C:35]([O:47][C:48](=[O:50])[CH3:49])[CH:34]=3)/[C:27](O)=[O:28])[N:25]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:67]1([CH:73]([O:80][C:81]([C:83]2[N:84]3[C@H:87]([S:88][CH2:89][C:90]=2[CH2:91][S:92][C:93]2[N:98]4[N:99]=[C:100]([C:102]([O:104][CH:105]([C:112]5[CH:117]=[CH:116][CH:115]=[CH:114][CH:113]=5)[C:106]5[CH:111]=[CH:110][CH:109]=[CH:108][CH:107]=5)=[O:103])[N:101]=[C:97]4[N:96]=[C:95]([CH3:118])[CH:94]=2)[C@H:86]([NH2:119])[C:85]3=[O:120])=[O:82])[C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:67]1([CH:73]([O:80][C:81]([C:83]2[N:84]3[C@H:87]([S:88][CH2:89][C:90]=2[CH2:91][S:92][C:93]2[N:98]4[N:99]=[C:100]([C:102]([O:104][CH:105]([C:112]5[CH:113]=[CH:114][CH:115]=[CH:116][CH:117]=5)[C:106]5[CH:107]=[CH:108][CH:109]=[CH:110][CH:111]=5)=[O:103])[N:101]=[C:97]4[N:96]=[C:95]([CH3:118])[CH:94]=2)[C@H:86]([NH:119][C:27](=[O:28])/[C:26](/[C:24]2[N:25]=[C:21]([NH:20][C:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[S:22][CH:23]=2)=[N:30]\[O:31][CH:32]([C:51]([O:53][CH:54]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[O:52])[C:33]2[CH:38]=[C:37]([O:39][C:40](=[O:42])[CH3:41])[C:36]([O:43][C:44](=[O:46])[CH3:45])=[C:35]([O:47][C:48](=[O:50])[CH3:49])[CH:34]=2)[C:85]3=[O:120])=[O:82])[C:74]2[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=2)[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1
Reactant: Cc1cc(SCC2=C(C(=O)OC(c3ccccc3)c3ccccc3)N3C(=O)[C@@H](N)[C@H]3SC2)n2nc(C(=O)OC(c3ccccc3)c3ccccc3)nc2n1
Reactant: CC(=O)Oc1cc(C(O/N=C(\C(=O)O)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)C(=O)OC(c2ccccc2)c2ccccc2)cc(OC(C)=O)c1OC(C)=O
Agent: C(=NC1CCCCC1)=NC1CCCCC1
Solvent: ClCCl
Product: CC(=O)Oc1cc(C(O/N=C(\C(=O)N[C@@H]2C(=O)N3C(C(=O)OC(c4ccccc4)c4ccccc4)=C(CSc4cc(C)nc5nc(C(=O)OC(c6ccccc6)c6ccccc6)nn45)CS[C@H]23)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)C(=O)OC(c2ccccc2)c2ccccc2)cc(OC(C)=O)c1OC(C)=O
Temperature: 25 °C
Reaction time: 8 h

Procedure:
To an ice-cooled solution containing the product obtained in Step 4 (2.2 g) and (6R,7R)-7-amino-3-[(2-diphenylmethyloxycarbonyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester (1.84 g) in dichloromethane (65 ml) was added dicyclohexylcarbodiimide (0.59 g), and the mixture was stirred overnight at room temperature. The insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the insoluble matters were removed by filtration. The filtrate was washed with brine and dried over anhydrous sodium sulfate. The dried solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, giving 0.86 g (less polar form) and 0.94 g (more polar form) of the objective compound.