反应详情

To a solution of 4-(tert-butoxycarbonylamino)benzaldehyde (250 mg, 1.13 mmol, synthesized at Example 278 (1)) in 2.3 mL of dry N,N-dimethylformamide was added sodium hydride (59 mg, 55%, 1.4 mmol) under nitrogen at 0° C. After the reaction mixture was stirred at room temperature for 30 min, methyl iodide (105 μL, 1.69 mmol) was added with additional stirring overnight. After quench with saturated NH4Cl aqueous solution, the mixture was extracted with diethyl ether. The extract was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40) to obtain the title compound (210 mg, 79%).

1. customat 0° C
2. stirringwith additional stirring overnight
3. customAfter quench with saturated NH4Cl aqueous solution
4. extractionthe mixture was extracted with diethyl ether
5. washThe extract was washed with saturated NaHCO3 aqueous solution, brine
6. dry with materialdried over MgSO4
7. filtrationAfter filtration
8. concentrationthe filtrate was concentrated in vacuo
9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40)