Water → (4RS,5SR)-5-(4-fluorophenyl)-4-((5-(trifluoromethyl)-2-furanyl)methyl)-1,3-oxazolidine-2-one

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionic acid (2.33 g, 7.01 mmol) in tetrahydrofuran (60 ml) were added diphenylphosphoryl azide (1.66 ml, 7.71 mmol) and triethylamine (1.47 ml, 10.5 mmol) and the mixture was heated under reflux for 4 hrs. The reaction solution was allowed to stand at room temperature, water (50 ml) was added, and the mixture was extracted with ethyl acetate (100 ml×2). The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate-hexane to give (4RS,5SR)-5-(4-fluorophenyl)-4-((5-(trifluoromethyl)-2-furanyl)methyl)-1,3-oxazolidine-2-one (1.78 mg, 77%).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 4 hrs
3. customto stand at room temperature
4. extractionthe mixture was extracted with ethyl acetate (100 ml×2)
5. washThe extract was washed successively with water and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customevaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (ethyl acetate)
9. customrecrystallized from ethyl acetate-hexane

ORDレコード

ord-4af3deb38081428384fcf0bce2ba2acb

出典データセット

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06982348B2