Pyridine → HCID 23093540, 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 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) was further added, and stirred at room temperature for 1 hr. 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 the residue was dissolved in ethyl acetate (10 mL), followed by adding 4N hydrogen chloride-ethyl acetate solution (10 mL). After stirring at room temperature for 1 hr, diethyl ether (20 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 (1.99 g).

1. stirringstirred at room temperature for 1 hr
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. dissolutionthe residue was dissolved in ethyl acetate (10 mL)
6. additionby adding 4N hydrogen chloride-ethyl acetate solution (10 mL)
7. stirringAfter stirring at room temperature for 1 hr
8. additiondiethyl ether (20 mL) was added
9. filtrationthe depositting solid was collected by filtration
10. washThe solid was washed twice with ethyl acetate (15 mL)
11. customdried at 60° C. under reduced pressure

ORD record

ord-178c7a87b26c4ee4aeb339b10eb74b6e

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08449911B2