Pyridine → HCID 23071203, compound

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (20 mL) were added pyridine (0.97 mL) and 4-dimethylaminopyridine (catalytic amount), and ethyl chlorocarbonate (1.25 mL) was dropwise added. The mixture was stirred overnight at room temperature and ethyl acetate (50 mL) was added. The mixture was washed with water (50 mL), a 5% aqueous citric acid solution (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., diethyl ether (10 mL) was added, and the precipitated solid was collected by filtration. The solid was dried under reduced pressure to give the title compound (1.66 g) as a white solid.

1. additionwas dropwise added
2. washThe mixture was washed with water (50 mL)
3. dry with materiala 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate
4. concentrationAfter concentration under reduced pressure
5. additiona 4N hydrogen chloride—ethyl acetate solution (10 mL) was added to the residue
6. stirringAfter stirring at room temperature for 2 hrs
7. addition, diethyl ether (10 mL) was added
8. filtrationthe precipitated solid was collected by filtration
9. customThe solid was dried under reduced pressure

ORD record

ord-0c761bb4364747198cbf7cb55b9595f6

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08980322B2