CCN(C(C)C)C(C)C.[F:10][CH2:11][CH2:12][N:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16](=[O:25])[C:15]([C:26]([OH:28])=O)=[CH:14]1.CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.[NH2:56][C:57]1[CH:62]=[CH:61][C:60]([C:63]2[C:64]([NH2:85])=[N:65][CH:66]=[C:67]([C:69]3[CH:74]=[CH:73][C:72]([O:75][CH2:76][C@H:77]4[CH2:82][O:81][CH2:80][CH2:79][O:78]4)=[C:71]([O:83][CH3:84])[CH:70]=3)[CH:68]=2)=[CH:59][CH:58]=1>CN(C=O)C.O>[NH2:85][C:64]1[C:63]([C:60]2[CH:59]=[CH:58][C:57]([NH:56][C:26]([C:15]3[C:16](=[O:25])[C:17]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:18][N:13]([CH2:12][CH2:11][F:10])[CH:14]=3)=[O:28])=[CH:62][CH:61]=2)=[CH:68][C:67]([C:69]2[CH:74]=[CH:73][C:72]([O:75][CH2:76][C@H:77]3[CH2:82][O:81][CH2:80][CH2:79][O:78]3)=[C:71]([O:83][CH3:84])[CH:70]=2)=[CH:66][N:65]=1DIPEA (60 μl) was added to a solution of the compound obtained in Step 2 of Example 19 (50 mg) and COMU (96 mg) in DMF (3.0 ml) at room temperature, and the mixture was stirred for one hour. The compound obtained in Step 1 of Example 42 (70 mg) was added at room temperature. The mixture was stirred for five hours, followed by the addition of water. The organic layer was extracted with ethyl acetate, and then washed with water and brine and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=19:1->9:1 (v/v)] to give 87 mg of the title compound as a solid.
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