[CH2:1]([O:3][C:4]([N:6]([CH2:14][C:15]([OH:17])=O)[CH2:7][CH2:8][C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)=[O:5])[CH3:2].CN(C=O)C.C(Cl)(=O)C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH2:14][C:15](=[O:17])[C:13]2[CH:12]=[CH:11][S:10][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]The product of step (b) (˜165 mmol, ˜42 g) was dissolved in 1 L of DCM. DMF (100 uL) was added followed slowly by oxalyl chloride (21.7 mL, 247 mmol). After 1 hour, the reaction was concentrated to dryness and the crude material was re-dissolved in DCE (1 L). AlCl3 (55 g, 410 mmol) was carefully added and the reaction was stirred at room temperature for ½ hour. The crude reaction was quenched with ice, washed with water (3×), and dried over MgSO4. The title product was purified by silica gel chromatography (30% EtOAc in Hexanes) to give 10.5 grams of the sub-title compound as a white solid. MS: ESI (positive): 240 (M+H).
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