反应详情

A flask is charged with a suspension of sodium hydride (60% in mineral oil) (0.109 g, 2.72 mmol) in THF (5 mL). The ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylate (0.735 g, 2.70 mmol) is added, followed by iodomethane (175 μL, 2.70 mmol) and the resulting suspension is heated to reflux for 3 hr, then cooled to rt. Water is added, followed by 1.0 N NaOH. The basic phase is extracted with 3 portions of EtOAc. The combined organic phases are washed with brine, dried over Na2SO4, filtered, and concentrated to give a clear oil purified with flash chromatography to give ethyl 2-[(tert-butoxycarbonyl)(methyl)amino]-1,3-thiazole-5-carboxylate. Yield 45%. HRMS (FAB) calculated for C12H18N2O4S+H 287.1065, found 287.1068.

1. temperaturethe resulting suspension is heated
2. temperatureto reflux for 3 hr
3. extractionThe basic phase is extracted with 3 portions of EtOAc
4. washThe combined organic phases are washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customto give a clear oil
9. custompurified with flash chromatography