C([C:4]1[CH:8]=[C:7](Cl)[S:6][C:5]=1[S:10]([NH:13][C:14]1[CH:19]=CC(CCO)=C[CH:15]=1)(=[O:12])=[O:11])(=O)C.[H-].[Na+].[CH3:25][O:26][CH2:27][CH2:28][CH2:29]Br>CN(C=O)C>[CH3:25][O:26][CH2:27][CH2:28][CH2:29][N:13]1[CH:14]([CH3:15])[CH2:19][C:4]2[CH:8]=[CH:7][S:6][C:5]=2[S:10]1(=[O:11])=[O:12]The product from Step B (800 mg, 3.95 mmol) was dissolved in DMF (10 mL) and the solution was cooled to -20° C. Sodium hydride (236 mg of an oil dispersion, 5.91 mmol) was added followed by 3-methoxypropyl bromide (1.8 mL, 11.82 mmol) and this mixture was warmed to 0° C. and stirred for 4 hr. The reaction mixture was poured into ice/water (50 mL) and extracted with ethyl acetate (2×100 mL). The combined extracts were washed with water (2×50 mL) and brine (2×50 mL), dried (MgSO4) and evaporated to an oil which was purified by column chromatography (silica, 10% methanol/methylene chloride) to give the desired product (890 mg, 82%).
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