Pyridine → HCID 23093484, compound

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Synthetic 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 reaction solution was stirred at 60° C. for 6 hrs. To the reaction solution was added ethyl acetate (80 mL), and washed sequentially with water (20 mL), saturated aqueous solution of sodium bicarbonate (20 mL) and water (20 mL), and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and to the residue was added 4N hydrogen chloride-ethyl acetate solution (10 mL). After stirring at room temperature for 22 hrs, diethyl ether (15 mL) was added, and the depositting solid was collected by filtration. The solid was washed twice with ethyl acetate (15 mL), and dried at 60° C. under reduced pressure to give title compound as white solid (2.01 g).

1. stirringthe reaction solution was stirred at 60° C. for 6 hrs
2. washwashed sequentially with water (20 mL), saturated aqueous solution of sodium bicarbonate (20 mL) and water (20 mL)
3. dry with materialdried over anhydrous magnesium sulfate
4. concentrationThe solution was concentrated under reduced pressure
5. additionto the residue was added 4N hydrogen chloride-ethyl acetate solution (10 mL)
6. stirringAfter stirring at room temperature for 22 hrs
7. additiondiethyl ether (15 mL) was added
8. filtrationthe depositting solid was collected by filtration
9. washThe solid was washed twice with ethyl acetate (15 mL)
10. customdried at 60° C. under reduced pressure

ORD record

ord-267b8ffb59d54248b7ce0f8b3cabf93e

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08449911B2