反应详情

A solution of 3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-N-[4-(trifluoromethyl)phenyl]benzamide (215 mg, 0.50 mmol) produced in Example A25(v), 2-chloro-2-oxoethyl acetate (273 mg, 2.00 mmol) and N-ethyl-N-isopropylpropane-2-amine (518 mg, 4.00 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 18 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was dissolved in methanol (5 mL)/tetrahydrofuran (5 mL), 8N aqueous sodium hydroxide solution (1 mL) was added under ice-cooling, and the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1), and triturated with diethyl ether to give the title compound (140 mg, 57%) as a pale-yellow solid.

1. extractionthe mixture was extracted with ethyl acetate
2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
3. customthe solvent was evaporated under reduced pressure
4. dissolutionThe residue was dissolved in methanol (5 mL)/tetrahydrofuran (5 mL), 8N aqueous sodium hydroxide solution (1 mL)
5. additionwas added under ice-
6. temperaturecooling
7. stirringthe mixture was stirred at room temperature for 30 min
8. additionThe reaction mixture was poured into water
9. extractionthe mixture was extracted with ethyl acetate
10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
11. customthe solvent was evaporated under reduced pressure
12. customThe residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1)
13. customtriturated with diethyl ether