Pyridine → HCID 23103062, 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 benzyl chlorocarbonate (1.57 mL) was dropwise added. After stirring at room temperature for 2 hrs., pyridine (0.65 mL) and benzyl chlorocarbonate (1.28 mL) were added. After stirring at room temperature for 5 days, pyridine (0.81 mL) was added under ice-cooling and a solution (5 mL) of benzyl chlorocarbonate (1.43 mL) in ethyl acetate was dropwise added slowly. After stirring at room temperature for 2 hrs., ethyl acetate (50 mL) was added to the mixture. 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 (1.99 g) as a white solid.

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

ORD record

ord-0a889c1551614ce7a827376ae26fc0de

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08980322B2