C(Cl)(=O)C(Cl)=O.CS(C)=O.[O:11]1[C:15]2[CH2:16][N:17]([S:20]([C:23]3[CH:30]=[CH:29][C:26]([CH2:27][OH:28])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:18][CH2:19][C:14]=2[CH:13]=[CH:12]1.C(N(CC)CC)C>ClCCl.C(OCC)C>[O:11]1[C:15]2[CH2:16][N:17]([S:20]([C:23]3[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:18][CH2:19][C:14]=2[CH:13]=[CH:12]1To a solution of 1.07 g (8.44 mmol) of oxalyl chloride in 50 ml of dichloromethane, 1.20 ml (16.9 mmol) of dimethyl sulfoxide was added dropwise at -78° C., followed by stirring for 5 minutes. To this solution, a solution of 1.650 g of the above crude 4-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-ylsulfonyl)benzyl alcohol in 10 ml of dichloromethane was added at -78° C., followed by stirring for 15 minutes. To this mixture, 4.70 ml (33.7 mmol) of triethylamine was added; the mixture was allowed to warm to room temperature. The reaction mixture was diluted with diethyl ether, washed with water and dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (dichloromethane) and crystallized from diethyl ether-hexane to yield the desired product.
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