C(N(CC)CC)C.[CH2:8]1[NH:15][CH2:14][CH:13]2[CH:9]1[CH2:10][C:11]1[CH:18]=[CH:17][S:16][C:12]=12.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(Cl)Cl.[Cl-].[Na+].O>[CH2:23]([O:22][C:20]([N:15]1[CH2:14][CH:13]2[CH:9]([CH2:10][C:11]3[CH:18]=[CH:17][S:16][C:12]=32)[CH2:8]1)=[O:21])[CH3:24]Triethylamine (741 mg, 7.32 mmol) was added to a solution of the product from step h) (493 mg, 2.44 mmol) in 12 mL of CH2Cl2 at ° C. followed by the addition of ethyl chloroformate (529 mg, 4.88 mmol). The reaction was allowed to come to room temperature and was stirred for two hours. The reaction mixture was diluted with brine (15 mL) and extracted with dichloromethane (3×15 mL). The combined organic extracts were dried with MgSO4 and the solvent was evaporated in vacuo give the crude product that was purified by column chromatography (SiO2) using a 0-30% ethyl acetate-hexane gradient to give the subtitle compound. MS calculated for C12H15NO2S+H: 238, observed: 238.
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