Hydrochloric Acid → HCID 67777697, compound

A mixture of methyl 3-[(2-hydroxybut-3-en-1-yl)oxy]isoxazole-5-carboxylate (2.71 g), t-butyldimethylsilyl trifluoromethanesulfonate (4.03 g), 2,6-dimethylpyridine (1.64 g) and THF (30 mL) was stirred at room temperature for 2 hr. To the reaction mixture was added 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, and then saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was mixed with tetraoxide osmium (7% immobilized catalyst, 2.31 g), sodium periodate (13.6 g), acetonitrile (30 mL), acetone (30 mL) and water (20 mL), and the obtained mixture was stirred at room temperature for 3 days. The precipitate was removed by filtration, and the filtrate was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was mixed with toluene (20 mL), diethylaminosulfur trifluoride (5.04 mL) was slowly added dropwise thereto at room temperature, and the obtained mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was mixed with THF (20 mL), tetrabutylammonium fluoride (1.0M THF solution, 25.4 mL) was slowly added dropwise thereto at 0° C., and the obtained mixture was stirred at 0° C. for 30 min. To the reaction mixture was added 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a white powder (370 mg).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate solution
3. dry with materialsaturated brine, and dried over anhydrous magnesium sulfate
4. customthe solvent was evaporated under reduced pressure
5. additionThe residue was mixed with tetraoxide osmium (7% immobilized catalyst, 2.31 g), sodium periodate (13.6 g), acetonitrile (30 mL), acetone (30 mL) and water (20 mL)
6. stirringthe obtained mixture was stirred at room temperature for 3 days
7. customThe precipitate was removed by filtration
8. extractionthe filtrate was extracted with ethyl acetate
9. washThe obtained organic layer was washed with saturated brine
10. dry with materialdried over anhydrous magnesium sulfate
11. customthe solvent was evaporated under reduced pressure
12. additionThe residue was mixed with toluene (20 mL), diethylaminosulfur trifluoride (5.04 mL)
13. additionwas slowly added dropwise
14. stirringat room temperature, and the obtained mixture was stirred at room temperature for 2 hr
15. additionTo the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution
16. extractionthe mixture was extracted with ethyl acetate
17. washThe obtained organic layer was washed with saturated brine
18. dry with materialdried over anhydrous magnesium sulfate
19. customthe solvent was evaporated under reduced pressure
20. additionThe residue was mixed with THF (20 mL), tetrabutylammonium fluoride (1.0M THF solution, 25.4 mL)
21. additionwas slowly added dropwise
22. stirringat 0° C., and the obtained mixture was stirred at 0° C. for 30 min
23. additionTo the reaction mixture was added 1M hydrochloric acid
24. extractionthe mixture was extracted with ethyl acetate
25. washThe obtained organic layer was washed with saturated brine
26. dry with materialdried over anhydrous magnesium sulfate
27. customthe solvent was evaporated under reduced pressure
28. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-978c80a5f6354b22b2635b85e3878a14

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729102B2