反应详情

A solution of methyl (2E)-3-(3-{1-[(tert-butoxycarbonyl)amino]ethyl}-5-chloro-2-methoxy-6-methylphenyl)acrylate (1.5 g, 3.9 mmol) in nitromethane (11 mL) at 0° C. was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (0.59 mL, 3.9 mmol) and allowed to warm to room temperature. The reaction mixture was heated at 60° C. for 21 h, cooled to room temperature, poured into water (100 ml) and extracted with EtOAc (2×75 mL). The organic layer was separated, washed with brine solution, dried over anhydrous sodium sulfate, filtered, and concentrated to give a orange foam. The crude material was dissolved in dichloromethane and purified by flash column chromatography using EtOAc in hexanes (0%-30% over 30 min) to give the desired product (0.93 g, 53%) as a white foam. LCMS for C20H29ClN2O7Na (M+Na)+: m/z=467.2. Found: 467.1.

1. temperatureThe reaction mixture was heated at 60° C. for 21 h
2. temperaturecooled to room temperature
3. extractionextracted with EtOAc (2×75 mL)
4. customThe organic layer was separated
5. washwashed with brine solution
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customto give a orange foam
10. custompurified by flash column chromatography
11. customEtOAc in hexanes (0%-30% over 30 min)