[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(OC([NH:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[CH:17][N:18]2[CH:23]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:24]([O:26][CH3:27])=[O:25])=O)(C)(C)C.C(N(CC)CC)C.O>C(Cl)Cl>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([CH:23]([N:18]2[C:19]3[C:15](=[C:14]([NH:13][S:2]([CH3:1])(=[O:4])=[O:3])[CH:22]=[CH:21][CH:20]=3)[CH:16]=[CH:17]2)[C:24]([O:26][CH3:27])=[O:25])=[CH:33][CH:32]=1Methanesulfonyl chloride (159 μL, 2.04 mmol) was added to a stirred solution of 2b (320 mg, 1.02 mmol) and triethylamine (213 μL, 1.53 mmol) in DCM (3 mL) at rt. After 1 h, the reaction mixture was poured into water and extracted with DCM. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier), followed by lyophilization of the purified fractions to afford the title compound 17. m/z (ES) 393 (MH)+ IP=C rating.
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