Pyridine → HCID 23103069, compound

Temperature

60 °C

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 3,4,5-trimethoxybenzoyl chloride (2.54 g) and pyridine (0.97 mL). After stirring at 60° C. for 14 hrs., 3,4,5-trimethoxybenzoyl chloride (1.30 g), pyridine (0.97 mL) and ethyl acetate (10 mL) were added, and the mixture was stirred at 60° C. for 24 hrs. The reaction mixture was filtered and ethyl acetate (50 mL) and water (30 mL) were added to the filtrate. After partitioning, ethyl acetate layer was washed with 1N hydrochloric acid (30 mL), water (30 mL), an aqueous copper (II) sulfate solution (30 mL), water (30 mL) and saturated brine (30 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (eluted with ethyl acetate:hexane=1:1). A 4N hydrogen chloride—ethyl acetate solution (10 mL) was added to the purified product. After stirring at room temperature for 4 hrs, the mixture was concentrated under reduced pressure. Toluene (10 mL) was added, and the mixture was 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 the title compound (1.79 g) as a white solid.

1. stirringthe mixture was stirred at 60° C. for 24 hrs
2. filtrationThe reaction mixture was filtered
3. additionethyl acetate (50 mL) and water (30 mL) were added to the filtrate
4. customAfter partitioning
5. washethyl acetate layer was washed with 1N hydrochloric acid (30 mL), water (30 mL)
6. dry with materialan aqueous copper (II) sulfate solution (30 mL), water (30 mL) and saturated brine (30 mL), and dried over anhydrous magnesium sulfate
7. concentrationAfter concentration under reduced pressure
8. customthe residue was purified by silica gel column chromatography (eluted with ethyl acetate:hexane=1:1)
9. additionA 4N hydrogen chloride—ethyl acetate solution (10 mL) was added to the purified product
10. stirringAfter stirring at room temperature for 4 hrs
11. concentrationthe mixture was concentrated under reduced pressure
12. additionToluene (10 mL) was added
13. concentrationthe mixture was concentrated 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-30c69f3a7eca430cb4bceb99f6636cde

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08980322B2