Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(=O)CC.C(OCC)(=O)C>[OH-:5].[NH4+:23].[CH:14]1([C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:7][CH:8]=2)=[O:13])[CH2:16][CH2:15]1A mixture of Example 1B (10 g, 42 mmol), KI (8.5 g, 51.2 mmol), K2CO3 (8.75 g, 63.3 mmol), and piperazine (10.75 g, 125 mmol) in 2-butanone (500 mL) was refluxed for 48 hours. The reaction mixture was then cooled to room temperature, treated with 1 M sodium thiosulfate (100 mL) and ethyl acetate (500 mL). The layers were separated, and the organic layer was washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by column chromatography on silica gel using 98:2:0.1 to 95:5:0.9 dichloromethane:methanol:concentrated ammonium hydroxide as the eluant to afford 9.931 g (82%) of the desired product.
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