反应详情

温度

40 °C

2 g of 4-[5-(4-Fluorophenyl)-1-(4-fluorophenylamino)-5-hydroxy-2-(2-oxo-4-phenyl-oxazolidine-3-carbonyl)-pentyl]-benzonitrile were dissolved in 20 ml of methyl-tert-butyl ether and, together with 100 mg of tetrabutylammonium fluoride trihydrate and 1.3 ml of bistrimethylsilyl acetamide, heated at 40° C. for about 1 h. The reaction was monitored by thin-layer chromatography. After the reaction ended, 0.2 ml of glacial acetic acid were initially added and the mixture was stirred for 30 min and then concentrated. 20 ml of a mixture of isopropanol/2N sulfuric acid=10:1 were added to the residue, and the mixture was stirred for 1 hour. Following addition of a spatula tip of solid sodium bicarbonate, the mixture was again concentrated under reduced pressure. The residue was taken up in ethyl acetate and the organic phase was washed with water and dried. The residue was, after removal of the solvent, purified by column chromatography (SiO2, CH2Cl2/methanol=100:1). This gave the product of molecular weight 418.45 (C25H20F2N2O2); MS (DCI+) 419 (M+H+).

1. concentrationconcentrated
2. addition20 ml of a mixture of isopropanol/2N sulfuric acid=10:1 were added to the residue
3. stirringthe mixture was stirred for 1 hour
4. additionaddition of a spatula tip of solid sodium bicarbonate
5. concentrationthe mixture was again concentrated under reduced pressure
6. washthe organic phase was washed with water
7. customdried
8. customafter removal of the solvent
9. custompurified by column chromatography (SiO2, CH2Cl2/methanol=100:1)
10. customThis gave the product of molecular weight 418.45 (C25H20F2N2O2)