[OH:1][CH:2]1[CH2:16][CH:5]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH:4]2[CH2:3]1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:17][S:18]([O:1][CH:2]1[CH2:16][CH:5]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:8][CH:4]2[CH2:3]1)(=[O:20])=[O:19]To a solution of the title compound from Step A above (550 mg, 2.4 mmol) and DMAP (296 mg) in DCM (15 mL) was added MsCl (189 μL) at 0° C. The mixture was stirred for 10 min at the same temperature and for an additional hour at RT. The mixture was quenched with ice water and extracted with ethyl acetate (2×50 mL). The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under vacuum. The residue oil was purified via prep-plate purification eluting with 50% ethyl acetate in hexane to afford the title compound (i-39) (555 mg, 75%). ESI-MS calculated for C13H23NO5S: Exact Mass: 305.13. Found 328.14 (MNa)+.
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