Pyridine → HCID 23103059, compound

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (10 mL) were added 4-fluorobenzoyl chloride (1.74 g) and pyridine (0.97 mL). The mixture was stirred at room temperature for 6.5 hrs. Ethyl acetate (80 mL) was added to the reaction mixture, and the mixture was washed with water (30 mL), a saturated aqueous sodium hydrogen carbonate solution (30 mL), water (30 mL) and saturated brine (30 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, a 4N hydrogen chloride—ethyl acetate solution (10 mL) was added to the residue. After stirring at room temperature for 1 hr., the precipitated solid was collected by filtration. The solid was washed twice with ethyl acetate (15 mL) and dried under reduced pressure at 60° C. to give the title compound (1.89 g) as a white solid.

1. washthe mixture was washed with water (30 mL)
2. dry with materiala saturated aqueous sodium hydrogen carbonate solution (30 mL), water (30 mL) and saturated brine (30 mL), and dried over anhydrous magnesium sulfate
3. concentrationAfter concentration under reduced pressure
4. additiona 4N hydrogen chloride—ethyl acetate solution (10 mL) was added to the residue
5. stirringAfter stirring at room temperature for 1 hr
6. filtration, the precipitated solid was collected by filtration
7. washThe solid was washed twice with ethyl acetate (15 mL)
8. customdried under reduced pressure at 60° C.

ORD record

ord-184411d505e74416bc29a78cb99ad398

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08980322B2