Water → HCID 23103056, compound

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (20 mL) was added pyridine (1.62 mL) and a solution (5 mL) of 2-methoxyethyl chlorocarbonate (2.77 g) in ethyl acetate was dropwise added slowly, and the mixture was stirred overnight at room temperature. After concentration of the reaction mixture under reduced pressure, water (50 mL) was added, the mixture was extracted with ethyl acetate (50 mL). The mixture was washed with 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was dissolved in diethyl ether (2 mL), and a 4N hydrogen chloride-ethyl acetate solution (5 mL) was added. After stirring at room temperature for 30 min., diethyl ether (10 mL) was added, and the mixture was stirred overnight. The precipitated solid was collected by filtration, and dried under reduced pressure to give the title compound (1.56 g) as a white solid.

1. extractionthe mixture was extracted with ethyl acetate (50 mL)
2. washThe mixture was washed with 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL)
3. dry with materialdried over anhydrous magnesium sulfate
4. concentrationAfter concentration under reduced pressure
5. dissolutionthe residue was dissolved in diethyl ether (2 mL)
6. additiona 4N hydrogen chloride-ethyl acetate solution (5 mL) was added
7. stirringAfter stirring at room temperature for 30 min.
8. additiondiethyl ether (10 mL) was added
9. stirringthe mixture was stirred overnight
10. filtrationThe precipitated solid was collected by filtration
11. customdried under reduced pressure

ORD record

ord-f6839dc0522f4e0e86289d0905ccafe5

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722084B2