4-[4-(4-Tert-butylphenylamino)phenoxy]-6-methoxyquinolin-7-ol (compound 21) (230 mg) was dissolved in N,N-dimethylformamide (8 ml) to prepare a solution. Potassium carbonate (300 mg) and p-toluenesulfonic acid (2R)-(−)-glycidyl (0.22 g) were then added to the solution, and the mixture was stirred at room temperature overnight. Morpholine (0.5 ml) was added to the reaction solution, and the mixture was further stirred at 70° C. overnight. Water and ethyl acetate were added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and was dried over sodium sulfate. The solvent was removed by evaporation under the reduced pressure, and the residue was purified by thin-layer chromatography on silica gel using chloroform/acetone for development to give the title compound (200 mg, yield 65%).
