[OH:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[NH:11][C:12]([CH:14]([N:19]1[CH2:23][CH:22]([O:24][C:25]2[C:34]3[C:29](=[CH:30][C:31]([O:35][CH3:36])=[CH:32][CH:33]=3)[CH:28]=[C:27]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:26]=2)[CH2:21][CH:20]1[C:43]1([C:48](O)=[O:49])[CH2:45][CH:44]1[CH:46]=[CH2:47])[C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[C:51]1([S:57]([NH2:60])(=[O:59])=[O:58])C=CC=CC=1.C(N([CH:67]([CH3:69])[CH3:68])CC)(C)C.[CH2:70]1[CH2:74]N([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)C[CH2:71]1.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[OH:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[NH:11][C:12](=[O:13])[CH:14]([N:19]1[CH2:23][CH:22]([O:24][C:25]2[C:34]3[C:29](=[CH:30][C:31]([O:35][CH3:36])=[CH:32][CH:33]=3)[CH:28]=[C:27]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:26]=2)[CH2:21][CH:20]1[C:43]1([C:48]([NH:60][S:57]([CH2:51][C:68]2[CH:67]=[CH:69][CH:74]=[CH:70][CH:71]=2)(=[O:59])=[O:58])=[O:49])[CH2:45][CH:44]1[CH:46]=[CH2:47])[C:15]([CH3:16])([CH3:18])[CH3:17]To solution of 14 (25 mg, 0.033 mmol) in chloroform (1 mL) was added benzenesulfonamide (10.5 mg, 0.066 mmol) followed by diisopropylethylamine (34 μL, 0.197 mmol). The solution was stirred at RT for 10 min and then at −20° C. for 30 min. PyBOP (76 mg, 0.13 mmol) was then added as a solid. The solution was kept at −20° C. for 48 hours. The solution was then poured into aqueous NaHCO3 (sat.) and washed with water. The organic layer was dried, concentrated and subjected to purification by HPLC, affording the title compound as a white solid.
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