Pyridine → HCID 86600930, compound

To a mixture of tert-butyl (2,3-dihydroxypropyl)methylcarbamate (15.53 g) obtained in Reference Example 45 and ethyl acetate (100 mL) were added pyridine (18.35 mL) and ethyl chlorocarbonate (24.62 g) under ice-cooling, and the mixture was stirred at room temperature for 96 hrs. Ethyl acetate (300 mL) was added to the reaction mixture, and the mixture was washed with water (150 mL), an aqueous copper sulfate solution (100 mL), water (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (eluted with ethyl acetate:hexane=1:6). To the purified product was added a 4N hydrogen chloride-ethyl acetate solution (80 mL), and the mixture was stirred at room temperature for 3 hrs. Diethyl ether (200 mL) was added, and the precipitated solid was collected by filtration. The solid was dried under reduced pressure to give the title compound (5.93 g) as a white solid.

1. temperaturecooling
2. washthe mixture was washed with water (150 mL)
3. dry with materialan aqueous copper sulfate solution (100 mL), water (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate
4. concentrationAfter concentration under reduced pressure
5. customthe residue was purified by silica gel column chromatography (eluted with ethyl acetate:hexane=1:6)
6. additionTo the purified product was added a 4N hydrogen chloride-ethyl acetate solution (80 mL)
7. stirringthe mixture was stirred at room temperature for 3 hrs
8. additionDiethyl ether (200 mL) was added
9. filtrationthe precipitated solid was collected by filtration
10. customThe solid was dried under reduced pressure

ORD record

ord-8b693b427ad94b879928e5850eed7fa6

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722084B2