[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[CH2:12][O:11][S:10](=[O:14])(=[O:13])[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:16](I)[CH:17]=[CH2:18].[OH-].[Na+]>C(Cl)Cl>[CH2:18]([N:9]1[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)([CH3:15])[CH2:12][O:11][S:10]1(=[O:14])=[O:13])[CH:17]=[CH2:16]To a solution of 4-(3-bromophenyl)-4-methyl[1,2,3]-oxathiazolidine-2,2-dioxide (7.3 g, 25 mmol) in DCM (77 mL) was added allyl iodide (9.1 mL, 100 mmol, 4 eq), followed by BnBu3NCl (0.39 g, 1.3 mmol) and 40% NaOH (28 mL). The mixture was stirred at RT for 16 h. The organic layer was separated and the solvent was evaporated. Silica gel chromatography using 5-20% EtOAc/hexanes gave 8.3 g (100%) of 3-allyl-4-(3-bromophenyl)-4-methyl-[1,2,3]-oxathiazolidine-2,2-dioxide (DC5; R6=Me) as a colorless oil. 1H NMR (CDCl3) 7.64 (t, J=1.8 Hz, 1H), 7.46-7.54 (m, 2H), 7.31 (t, J=8.0 Hz, 1H), 5.77-5.89 (m, 1H), 5.19-5.33 (m, 2H), 4.38 (dd, J1=8.7 Hz, J2=23.7 Hz, 2H), 3.46-3.68 (m, 2H), 1.83 (s, 3H).
불러오는 중…
