[F:1][C@H:2]1[C@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C>ClCCl>[F:1][C@H:2]1[C@H:6]([O:7][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1(trans)-Benzyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate (2.0 g, 8.36 mmol) was added to dichloromethane and cooled to 0° C. Methanesulfonyl chloride (1.30 mL, 16.7 mmol) and triethylamine (2.3 mL, 16.7 mmol) were sequentially added, and the reaction was allowed to warm to ambient temperature overnight under vigorous stirring. The following day, additional dichloromethane was added, and the reaction mixture was washed with a saturated solution of NaHCO3. The combined organic layers were dried over MgSO4, filtered and evaporated. The crude oil was purified on silica gel using ethyl acetate and hexane to produce 2.0 g (70% isolated yield) of the desired product as an oil.
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