反应详情

温度

-10 °C

Under argon, 2.5 g of 3-[5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyloxazolidin-2-one were dissolved in 30 ml of dichloromethane. 3.9 g of 4-[(4-fluorophenylimino)-methyl]-benzonitrile were added and the mixture was cooled to −10° C. 6.4 ml of diisopropylethylamine and, over a period of 30 min, 4.05 ml of trimethylsilyl chloride were added to this mixture so that the temperature did not exceed −5° C. The mixture was stirred at this temperature for 1 additional hour and then cooled to −25° C. 0.8 ml of titanium tetrachloride were then added slowly. The dark mixture was stirred at a temperature ranging from −25 to −30° C. overnight and then decomposed using 35 ml of a 7 percent strength solution of tartaric acid and then stirred at room temperature for another hour. 15 ml of a 20 percent strength solution of sodium bicarbonate were then added, and the mixture was again stirred for 1 hour. Following magnesium sulfate and concentrated to about 10 ml. Following the addition of 2 ml of bistrimethylsilylacetamide, the mixture was heated at reflux for 30 min and then concentrated under reduced pressure. The residue was crystallized using ethyl acetate/heptane. The product was filtered off with suction and dried under reduced pressure. This gave the product of molecular weight 653.81 (C37H37F2N3O4Si); MS (ESI+): 654.3 (M+H+), 582.2 (M+H+—Si(CH3)3).

1. customdid not exceed −5° C
2. temperaturecooled to −25° C
3. stirringThe dark mixture was stirred at a temperature
4. stirringstirred at room temperature for another hour
5. stirringthe mixture was again stirred for 1 hour
6. concentrationFollowing magnesium sulfate and concentrated to about 10 ml
7. additionthe addition of 2 ml of bistrimethylsilylacetamide
8. temperaturethe mixture was heated
9. temperatureat reflux for 30 min
10. concentrationconcentrated under reduced pressure
11. customThe residue was crystallized
12. filtrationThe product was filtered off with suction
13. customdried under reduced pressure
14. customThis gave the product of molecular weight 653.81 (C37H37F2N3O4Si)