反应详情

温度

40 °C

4-{(2S)-3-Hydroxy-2-[(3-nitroquinolin-4-yl)amino]propyl}phenol (21.69 g, 64.5 mmol) was dissolved in 100 mL of dry pyridine and treated with tert-butyldimethylsilyl chloride (22.4 g, 148 mmol) and a catalytic amount of DMAP (0.79 g, 6.45 mmol). The reaction mixture was stirred under N2 and heated to 40° C. After 2.5 days, the reaction mixture was concentrated under reduced pressure. The resulting orange residue was partitioned between 200 mL of ethyl acetate and 200 mL of H2O. The layers were separated and the organic portion was washed sequentially with H2O and brine. The organic layer was then dried over Na2SO4, filtered, and concentrated under reduced pressure to give N-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-{[tert-butyl(dimethyl)silyl]oxy}benzyl)ethyl]-3-nitroquinolin-4-amine (25.24 g) as an orange solid.

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. customThe resulting orange residue was partitioned between 200 mL of ethyl acetate and 200 mL of H2O
3. customThe layers were separated
4. washthe organic portion was washed sequentially with H2O and brine
5. dry with materialThe organic layer was then dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure