Pyridine → HCID 23071203, 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) were added pyridine (0.97 mL) and 4 -dimethylaminopyridine (catalytic amount), and ethyl chlorocarbonate (1.25 mL) was added. After stirring overnight at room temperature, ethyl acetate (50 mL) was added to the reaction solution, and washed sequentially with water (50 mL), 5% aqueous solution of citric acid (50 mL), and saturated saline (50 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 2 hrs, diethyl ether (10 mL) was added thereto, and the depositting solid was collected by filtration. The solid was dried under reduced pressure to give title compound as white solid (1.66 g).

1. additionwas added
2. washwashed sequentially with water (50 mL), 5% aqueous solution of citric acid (50 mL), and saturated saline (50 mL)
3. dry with materialby drying 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 2 hrs
7. additiondiethyl ether (10 mL) was added
8. filtrationthe depositting solid was collected by filtration
9. customThe solid was dried under reduced pressure

ORD record

ord-e4bcf44944094362966ddd582c0f58ec

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08449911B2