Pyridine → HCID 23093484, 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 3-chlorobenzoyl chloride (1.92 g) and pyridine (0.97 mL). After stirring at room temperature for 1 hr., the mixture was stirred at 60° C. for 6 hrs. 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, a 4N hydrogen chloride-ethyl acetate solution (10 mL) was added to the residue. After stirring at room temperature for 22 hrs., diethyl ether (15 mL) was added, and the precipitated solid was collected by filtration.

1. stirring, the mixture was stirred at 60° C. for 6 hrs
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. additiona 4N hydrogen chloride-ethyl acetate solution (10 mL) was added to the residue
6. stirringAfter stirring at room temperature for 22 hrs
7. addition, diethyl ether (15 mL) was added
8. filtrationthe precipitated solid was collected by filtration

ORD record

ord-fdbeaab370d64ce7afe4534e157ca7cd

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722084B2