反应详情

温度

70 °C

To a solution of (S)-2-((tert-butoxycarbonyl)amino)butyl methanesulfonate (13.4 g, 50 mmol) in DMF (100 mL) was added sodium azide (6.5 g, 100 mmol). The reaction mixture was heated at 70° C. for 18 h. After cooling to rt, water was added, and the reaction mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. Purification by chromatography (SiO2; 0-50% EtOAc/hexanes) provided the desired product as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 6.87 (d, J=8.6 Hz, 1H), 3.54-3.37 (m, 1H), 3.27-3.20 (m, 2H), 1.45-1.25 (m, 2H), 1.39 (s, 9H), 0.82 (t, J=7.4 Hz, 3H).

1. temperatureAfter cooling to rt
2. extractionthe reaction mixture was extracted with EtOAc
3. washThe combined organic extracts were washed with brine
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customPurification by chromatography (SiO2; 0-50% EtOAc/hexanes)