Pyridine → HCID 23103059, 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-fluorobenzoyl chloride (1.74 g) and pyridine (0.97 mL). The reaction solution was stirred at room temperature for 6.5 hrs. Ethyl acetate (80 mL) was added to the reaction solution, and washed sequentially with water (30 mL), saturated aqueous solution of sodium bicarbonate (30 mL), water (30 mL) and saturated brine (30 mL), followed by drying 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 1 hr, 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 (1.89 g).

1. washwashed sequentially with water (30 mL), saturated aqueous solution of sodium bicarbonate (30 mL), water (30 mL) and saturated brine (30 mL)
2. dry with materialby drying over anhydrous magnesium sulfate
3. concentrationThe solution was concentrated under reduced pressure
4. additionto the residue was added 4N hydrogen chloride-ethyl acetate solution (10 mL)
5. stirringAfter stirring at room temperature for 1 hr
6. filtrationthe depositting solid was collected by filtration
7. washThe solid was washed twice with ethyl acetate (15 mL)
8. customdried at 60° C. under reduced pressure

ORD record

ord-4737973c695648e3a263a986b1c86d38

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08449911B2