Br[CH:2]([OH:4])[CH3:3].Cl[S:6]([N:9]=[C:10]=[O:11])(=[O:8])=[O:7].[CH:12]1([NH2:15])[CH2:14][CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[CH:12]1([NH:15][S:6]([N:9]2[CH2:3][CH2:2][O:4][C:10]2=[O:11])(=[O:8])=[O:7])[CH2:14][CH2:13]1
To a solution of bromoethanol (1 g, 8.06 mmol) in DCM was added chloro sulfonyl isocyanate (1.13 g, 8.06 mmol) in DCM and this solution added over 2 min, dropwise, to cyclopropyl amine (0.552 g, 0.009 mmol) and triethylamine (1 ml, 0.007 mmol) in DCM and stirred at RT for 1 h. The mixture was quenched with 0.2 M HCl solution and extracted with DCM (3×150 ml). The combined organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the product in 48% yield (0.8 g). 1H NMR (400 MHz, DMSO-d6): δ 8.15-8.14 (d, 1H), 4.42 (t, 2H), 3.70 (t, 2H), 2.35 (m, 1H), 0.58-0.53 (m, 4H).
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