4-Fluorobenzonitrile → HCID 67732715, compound

Temperature

50 °C

To a suspension of 200 mg of 60% sodium hydride in anhydrous N,N-dimethylformamide (1 ml) was added dropwise an N,N-dimethylformamide (7 ml) solution of 0.98 g of (4S, 5S)-(-)-3-(4-methoxyphenyl)-4-methyl-2-oxooxazolidin-5-ylmethyl alcohol obtained in Reference Example 11 at room temperature in a stream of nitrogen, and the mixture was stirred at 50° C. for 25 minutes. A solution of 500 mg of p-fluorobenzonitrile in anhydrous N,N-dimethylformamide (2 ml) was added thereto at the same temperature and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure and the obtained residue was extracted with ethyl acetate. The extract was washed with water, dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and purified by hexane-ethyl acetate gradient elution to give 0.98 g of the title compound (yield 70%).

1. customobtained in Reference Example 11 at room temperature in a stream of nitrogen
2. stirringat the same temperature and the mixture was stirred for 30 minutes
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. extractionthe obtained residue was extracted with ethyl acetate
5. washThe extract was washed with water
6. dry with materialdried with magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure
9. custompurified by hexane-ethyl acetate gradient elution

ORD record

ord-5db0bc9f6f0a4416a669623b84400af6

Source dataset

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05480899