Pyridine → HCID 23103054, compound

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (3.50 g) obtained in Reference Example 1 and ethyl acetate (20 mL) were added isopropyl chlorocarbonate (1.35 g) and pyridine (1.94 mL) under ice-cooling. After stirring under ice-cooling for 3.5 hrs., isopropyl chlorocarbonate (1.84 g) was added, and the mixture was stirred at room temperature for 2.5 hrs. Ethyl acetate (120 mL) was added to the reaction mixture, and the mixture was washed with water (50 mL) and saturated brine (50 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 2 hrs., the precipitated solid was collected by filtration. The solid was washed with ethyl acetate (15 mL), and dried under reduced pressure at 60° C. to give the title compound (1.38 g) as a white solid.

1. temperaturecooling
2. temperaturecooling for 3.5 hrs
3. stirringthe mixture was stirred at room temperature for 2.5 hrs
4. washthe mixture was washed with water (50 mL) and saturated brine (50 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationAfter concentration under reduced pressure
7. additiona 4N hydrogen chloride-ethyl acetate solution (10 mL) was added to the residue
8. stirringAfter stirring at room temperature for 2 hrs
9. filtration, the precipitated solid was collected by filtration
10. washThe solid was washed with ethyl acetate (15 mL)
11. customdried under reduced pressure at 60° C.

ORD record

ord-755fde1ed4cd4c66b8061702e745e01c

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722084B2