[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16]Br)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl.[F:29][C@H:30]1[CH2:34][CH2:33][NH:32][CH2:31]1>CN(C=O)C.CO.C(OCC)(=O)C.CCCCCC>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:32]2[CH2:33][CH2:34][C@H:30]([F:29])[CH2:31]2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]To a solution of tert-butyl{2-[4-(bromomethyl)phenyl]ethyl}carbamate (450 mg, 1.43 mmol) in DMF (4 ml) were added N,N-diisopropylethylamine (0.749 ml, 4.30 mmol) and (3S)-3-fluoropyrrolidine hydrochloride (180 mg, 1.43 mmol), and the mixture was stirred at room temperature for 22 hr. Ethyl acetate was added to the reaction mixture, and the mixture was washed with aqueous sodium hydrogen carbonate solution and brine. The solvent was evaporated under reduced pressure, and the residue was purified by NH-silica gel chromatography (developing solvent; ethyl acetate), and then silica gel chromatography (developing solvent; hexane:ethyl acetate=1:1 (volume ratio)→ethyl acetate:methanol=9:1 (volume ratio)) to give the title compound (364 mg, 1.13 mmol) as a colorless liquid.
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