反应详情

To a solution of the acid 12 (1.0 g, 2.8 mM) in benzene (25 ml) was added Et3N (0.39 ml, 2.8 mM) and diphenylphosphoryl azide (0.60 ml, 2.8 mM). After stirring overnight at room temperature, the reaction mixture was heated to 70° C. for 1.5 hours, cooled and concentrated in vacuo. Dioxane (2 ml), followed by a solution of concentrated HCl (0.3 ml) in dioxane (2 ml) was added, and the reaction mixture was heated to reflux for 2 hours, cooled and diluted to 50 ml with EtOAc. The organic solution was washed with a 0.25N NaOH solution, and extracted with 1N HCl. The extracts were combined, basified with 5N NaOH, and extracted with EtOAc, dried, filtered and concentrated in vacuo. Crystallization from Et2O afforded pure 42 (0.62 g, 68%) as a light yellow crystalline solid, mp=95°-97°. MS, m/e 327 (M+).

1. temperaturethe reaction mixture was heated to 70° C. for 1.5 hours
2. temperaturecooled
3. concentrationconcentrated in vacuo
4. additionwas added
5. temperaturethe reaction mixture was heated
6. temperatureto reflux for 2 hours
7. temperaturecooled
8. additiondiluted to 50 ml with EtOAc
9. washThe organic solution was washed with a 0.25N NaOH solution
10. extractionextracted with 1N HCl
11. extractionextracted with EtOAc
12. customdried
13. filtrationfiltered
14. concentrationconcentrated in vacuo
15. customCrystallization from Et2O afforded pure 42 (0.62 g, 68%) as a light yellow crystalline solid, mp=95°-97°