Pyridine → HCID 23103069, compound

Temperature

60 °C

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 3,4,5-trimethoxybenzoyl chloride (2.54 g) and pyridine (0.97 mL). After stirring at 60° C. for 14 hrs, to the reaction solution were further added 3,4,5-trimethoxybenzoyl chloride (1.30 g), pyridine (0.97 mL) and ethyl acetate (10 mL), and stirred at 60° C. for 24 hrs. The reaction solution was filtered, and to the filtrate were added ethyl acetate (50 mL) and water (30 mL). After separating the layers, the ethyl acetate layer was washed sequentially with 1 N hydrochloric acid (30 mL), water (30 mL), aqueous solution of copper (II) sulfate (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 the residue was purified by silica gel column chromatography (elute with ethyl acetate:hexane=1:1). To the purified materials was added 4N hydrogen chloride-ethyl acetate solution (10 mL). After stirring at room temperature for 4 hrs, the solution was concentrated under reduced pressure. Toluene (10 mL) was added to the residue, and concentrated under reduced pressure. The residue was suspended in ethyl acetate, and the solid was collected by filtration. After washing with ethyl acetate (15 mL), the solid was dried under reduced pressure to give title compound as white solid (1.79 g).

1. stirringstirred at 60° C. for 24 hrs
2. filtrationThe reaction solution was filtered
3. additionto the filtrate were added ethyl acetate (50 mL) and water (30 mL)
4. customAfter separating the layers
5. washthe ethyl acetate layer was washed sequentially with 1 N hydrochloric acid (30 mL), water (30 mL), aqueous solution of copper (II) sulfate (30 mL), water (30 mL) and saturated brine (30 mL)
6. dry with materialby drying over anhydrous magnesium sulfate
7. concentrationThe solution was concentrated under reduced pressure
8. customthe residue was purified by silica gel column chromatography (elute with ethyl acetate:hexane=1:1)
9. additionTo the purified materials was added 4N hydrogen chloride-ethyl acetate solution (10 mL)
10. stirringAfter stirring at room temperature for 4 hrs
11. concentrationthe solution was concentrated under reduced pressure
12. additionToluene (10 mL) was added to the residue
13. concentrationconcentrated under reduced pressure
14. filtrationthe solid was collected by filtration
15. washAfter washing with ethyl acetate (15 mL)
16. customthe solid was dried under reduced pressure

ORD record

ord-cd5192bfccac4aa08184d38407a1e3c0

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08449911B2