Potassium Hydroxide → (S)-4-(5-fluoro-2-methoxypyridin-3-yl)oxazolidin-2-one

Temperature

0 °C

To a solution of (S)-2-amino-2-(5-fluoro-2-methoxypyridin-3-yl)ethanol dihydrochloride (897 mg, 3.46 mmol) in KOH (10 mL, 24.2 mmol, 2.42 M in water) was added THF (10 mL). The mixture was cooled to 0° C. and treated with triphosgene (1.03 g, 3.46 mmol). The mixture was allowed to warm to ambient temperature with stirring over 16 hours then partitioned between EtOAc (50 mL) and water (50 mL), and the layers were separated. The aqueous layer was extracted with EtOAc (2×30 mL) and the combined organic phases were washed with brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was triturated with Et2O, filtered and dried under reduced pressure to afford (S)-4-(5-fluoro-2-methoxypyridin-3-yl)oxazolidin-2-one (254 mg, 35% yield) as a white powder. 1H NMR (CDCl3) δ 7.98 (m, 1H), 7.44 (m, 1H), 5.61 (Br S, 1H), 5.13 (m, 1H), 4.83 (m, 1H), 4.16 (m, 1H), 3.96 (s, 3H).

1. temperatureto warm to ambient temperature
2. customthen partitioned between EtOAc (50 mL) and water (50 mL)
3. customthe layers were separated
4. extractionThe aqueous layer was extracted with EtOAc (2×30 mL)
5. washthe combined organic phases were washed with brine (20 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was triturated with Et2O
10. filtrationfiltered
11. customdried under reduced pressure

ORD record

ord-ec502f11f5024dbca000e37471bfb75c

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933084B2