Pyridine → HCID 23093540, compound

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (10 mL) were added 4-methoxybenzoyl chloride (1.88 g) and pyridine (0.97 mL). After stirring at room temperature for 14 hrs., 4-methoxybenzoyl chloride (0.70 g) and pyridine (0.97 mL) were added and the mixture was stirred at room temperature for 1 hr. Ethyl acetate (80 mL) was added to the reaction mixture, and the mixture was washed with water (20 mL), a saturated aqueous sodium hydrogen carbonate solution (20 mL) and water (20 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was dissolved in ethyl acetate (10 mL), and a 4N hydrogen chloride—ethyl acetate solution (10 mL) was added. After stirring at room temperature for 1 hr., diethyl ether (20 mL) was added, and the precipitated solid was collected by filtration. The solid was washed twice with ethyl acetate (15 mL) and dried under reduced pressure at 60° C. to give the title compound (1.99 g) as a white solid.

1. stirringthe mixture was stirred at room temperature for 1 hr
2. washthe mixture was washed with water (20 mL)
3. dry with materiala saturated aqueous sodium hydrogen carbonate solution (20 mL) and water (20 mL), and dried over anhydrous magnesium sulfate
4. concentrationAfter concentration under reduced pressure
5. dissolutionthe residue was dissolved in ethyl acetate (10 mL)
6. additiona 4N hydrogen chloride—ethyl acetate solution (10 mL) was added
7. stirringAfter stirring at room temperature for 1 hr
8. addition, diethyl ether (20 mL) was added
9. filtrationthe precipitated solid was collected by filtration
10. washThe solid was washed twice with ethyl acetate (15 mL)
11. customdried under reduced pressure at 60° C.

ORD record

ord-3aa54c8bc9c14674937e7324e1cad4e6

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08980322B2