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, and the mixture was extracted with ethyl acetate (50 mL). The extract 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 extract 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-a9518faa57434861a6c016a6e70b3c7f

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08980322B2