反应详情

温度

0 °C

To a solution of NaH (0.57 g, 60%, 14.25 mmol) in 20 ml of THF at 0° C. was added S-3-(tert-butoxycarbonylamino)propyl ethanethioate (1.25 g, 5.36 mmol) under Ar. After stirring at 0° C. for 30 min, MeI (1.0 ml, 16.06 mmol) was added to the mixture. Stirring was continued at 0° C. for 2 h then RT overnight. The mixture was concentrated, redisolved in 120 ml of EtAc/Hexane (1:2), washed with 1 M NaH2PO4 NaCl (conc.), dried over MgSO4, filtered, evaporated and purified on SiO2 chromatography eluted with EtAc/Hexane (1:7) to afford 1.121 g (85%) of the title compound. 1H NMR (CDCl3) 3.69 (t, 2H, J=7.3 Hz), 2.41 (t, 2H, J=7.3 Hz), 2.39 (s, 3H), 2.03 (s, 3H), 1.76 (m, 2H),1.47 (s, 9H); 13C NMR 173.21, 153.39, 83.28, 43.67, 31.84, 28.26, 28.19, 27.11, 15.65; MS m/z+ 270.0 (M+Na).

1. stirringStirring
2. waitwas continued at 0° C. for 2 h
3. customRT overnight
4. concentrationThe mixture was concentrated
5. washwashed with 1 M NaH2PO4 NaCl (conc.)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated
9. custompurified on SiO2 chromatography
10. washeluted with EtAc/Hexane (1:7)