[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([O:16][CH3:17])=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[OH-].[Na+].CC(C)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:19]([N:6]1[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][C:9]([O:16][CH3:17])=[CH:10][CH:11]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]
A 50 mL flask was charged with 3.00 g (13.2 mmol) of compound 12, 5.10 g (26.4 mmol, Aldrich Co.) of 1-bromooctane, 1.06 g (26.4 mmol) of sodium hydroxide reagent grade, 134 mg (0.39 mmol) of tetrabutylamonium hydrogensulfate (TBAH) and 25 mL of anhydrous acetone. The resulting mixture was refluxed under argon for 24 h and then poured into 100 mL of distillated water. The aqueous layer was extracted three times with diethyl ether. The combined organic fractions were dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified by column chromatography (silica gel, 5% ethyl acetate in hexanes as eluent) to provide 4.06 g of the title product as white fluffy solid. M.P. 63-64° C. (Yield: 91%).
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