Pyridine → HCID 23093561, compound

To a mixture of tert-butyl 2-hydroxyethyl (methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (10 mL) were added methoxyacetyl chloride (1.20 g) and pyridine (0.97 mL). After stirring at room temperature for 3 hrs., ethyl acetate (70 mL) was added to the reaction mixture. The mixture was washed with water (20 mL), a saturated aqueous sodium hydrogen carbonate solution (20 mL) and water (20 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was dissolved in ethyl acetate (5 mL), and a 4N hydrogen chloride-ethyl acetate solution (10 mL) was added. After stirring at room temperature for 1 hr., the mixture was concentrated under reduced pressure. Water (60 mL) and diethyl ether (30 mL) were added to the residue. After stirring, the aqueous layer was separated and taken. The aqueous layer was basified with sodium hydrogen carbonate and extracted twice with ethyl acetate (40 mL). The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (1.00 g) as a colorless oil.

1. washThe mixture was washed with water (20 mL)
2. dry with materiala saturated aqueous sodium hydrogen carbonate solution (20 mL) and water (20 mL), and dried over anhydrous magnesium sulfate
3. concentrationAfter concentration under reduced pressure
4. dissolutionthe residue was dissolved in ethyl acetate (5 mL)
5. additiona 4N hydrogen chloride-ethyl acetate solution (10 mL) was added
6. stirringAfter stirring at room temperature for 1 hr
7. concentration, the mixture was concentrated under reduced pressure
8. additionWater (60 mL) and diethyl ether (30 mL) were added to the residue
9. stirringAfter stirring
10. customthe aqueous layer was separated
11. extractionextracted twice with ethyl acetate (40 mL)
12. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
13. concentrationconcentrated under reduced pressure

ORD record

ord-50e0348d8ce84ec196b06c4792a47095

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722084B2