Water → HCID 59389363, compound

The compound of Example 41 (4.53 g) was dissolved in dichloromethane (50 mL). The solution was kept at 0° C. and boron tribromide (21.6 mL, 1.0 mol/L dichloromethane solution) was added. The resulting mixture was stirred for 1 hour. Subsequently, water was added and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The resulting solid product (4.29 g) was dissolved in ethanol (40 mL). To this solution, water (40 mL) and potassium hydroxide (4.10 g) were added and the mixture was stirred for 2 hours under reflux. This was followed by addition of water and concentrated hydrochloric acid to make the mixture acidic. The resulting mixture was extracted with three times with ethyl acetate and the organic layer was washed with saturated brine, dried over sodium sulfate and filtered. The solvent was evaporated under reduced pressure. The resulting solid product (3.58 g) was dissolved in ethanol (100 mL). To this solution, concentrated sulfuric acid (2 mL) was added and the mixture was refluxed for 7.5 hours. Subsequently, ethanol was evaporated under reduced pressure and the residue was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford the title compound as a gray powder (2.88 g) (Process B).

1. customwas kept at 0° C.
2. extractionthe mixture was extracted three times with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over sodium sulfate
5. customThe solvent was evaporated under reduced pressure
6. dissolutionThe resulting solid product (4.29 g) was dissolved in ethanol (40 mL)
7. additionTo this solution, water (40 mL) and potassium hydroxide (4.10 g) were added
8. stirringthe mixture was stirred for 2 hours
9. temperatureunder reflux
10. additionThis was followed by addition of water and concentrated hydrochloric acid
11. extractionThe resulting mixture was extracted with three times with ethyl acetate
12. washthe organic layer was washed with saturated brine
13. dry with materialdried over sodium sulfate
14. filtrationfiltered
15. customThe solvent was evaporated under reduced pressure
16. dissolutionThe resulting solid product (3.58 g) was dissolved in ethanol (100 mL)
17. additionTo this solution, concentrated sulfuric acid (2 mL) was added
18. temperaturethe mixture was refluxed for 7.5 hours
19. customSubsequently, ethanol was evaporated under reduced pressure
20. extractionthe residue was extracted three times with ethyl acetate
21. washThe organic layer was washed with saturated brine
22. dry with materialdried over sodium sulfate
23. customThe solvent was evaporated under reduced pressure

ORD record

ord-c8690efe0a6d4e59a08e96fb1064b195

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763617B2