Pyridine → HCID 23103056, compound

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Synthetic Example 1 and ethyl acetate (20 mL) was added pyridine (1.62 mL), and a solution of 2-methoxyethyl chlorocarbonate (2.77 mL) in ethyl acetate (5 mL) was slowly added dropwise, followed by stirring at room temperature overnight. The reaction solution was concentrated under reduced pressure, and extracted with ethyl acetate (50 mL). The extract was washed with 5% aqueous solution of citric acid (50 mL), and saturated saline (50 mL), and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was dissolved in diethyl ether (2 mL), and added 4N hydrogen chloride-ethyl acetate solution (5 mL). After stirring at room temperature for 30 minutes, diethyl ether (10 mL) was added, and stirred overnight. The depositting solid was collected by filtration, and dried under reduced pressure to give title compound as white solid (1.56 g).

1. concentrationThe reaction solution was concentrated under reduced pressure
2. extractionextracted with ethyl acetate (50 mL)
3. washThe extract was washed with 5% aqueous solution of citric acid (50 mL), and saturated saline (50 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationThe solution was concentrated under reduced pressure
6. dissolutionthe residue was dissolved in diethyl ether (2 mL)
7. additionadded 4N hydrogen chloride-ethyl acetate solution (5 mL)
8. stirringAfter stirring at room temperature for 30 minutes
9. additiondiethyl ether (10 mL) was added
10. stirringstirred overnight
11. filtrationThe depositting solid was collected by filtration
12. customdried under reduced pressure

ORD record

ord-349f54050bb541009dfe17b9c5319f73

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08449911B2