[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2]C.[CH2:8]([O:15][C@H:16]1[CH2:20][CH2:19][CH2:18][C@@H:17]1[NH2:21])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:22]1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH3:22][CH:1]([S:4]([NH:21][CH:17]1[CH2:18][CH2:19][CH2:20][CH:16]1[O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:5])=[O:6])[CH3:2]Scheme IA, step A: In a 250 mL 3 neck flask fitted with a stirrer and thermometer, propanesulfonyl chloride (4.47 g, 1.2 eq) was added dropwise to (1S,2S)-2-benzyloxycyclopentylamine (5.00 g, 10 mmol) and DBU (5.98 g, 1.5 eq) in CH2Cl2 (100 mL) while stirring at 0° C. under a nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred overnight at this temperature. In the morning, the reaction was diluted with CH2Cl2 (100 mL) and the organic layer was washed two times with H2O, dried over Na2SO4, filtered, and concentrated under reduced vacuum to yield 10.13 g as a viscous oil. This material was purified via silica gel chromatography employing the Water's Prep. 2000 and eluting with a solvent of hexane/ethyl acetate 4:1 to yield the intermediate title compound (8.0 g, 95%) as a white solid. Ion spray M.S. 296 (M*−1). Analysis calculated for C15H23NO3S: Theory: C, 60.58; H, 7.80; N, 4.71. Found: C, 60.39; H, 7.79; N, 4.73.
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