Potassium Carbonate → Ethyl 2-amino-7-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]hept-6-ynoate

Temperature

80 °C

A mixture of 5-[4-(5-chloropent-1-yn-1-yl)-2-methoxyphenyl]-2-methyl-1,3-oxazole (500 mg), ethyl N-(diphenylmethylene)glycinate (461 mg), potassium carbonate (1.2 g) and tetrabutylammonium iodide (637 mg) in acetonitrile (5 mL) was stirred at 80° C. overnight under an argon atmosphere. The reaction mixture was diluted with ethyl acetate, the mixture was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, the insoluble material was separated by filtration, and the filtrate was concentrated. A mixture of the residue and 6N hydrochloric acid (0.5 mL) in acetonitrile (5 mL) was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (362 mg).

1. washthe mixture was washed with water and saturated brine
2. dry with materialdried over anhydrous sodium sulfate
3. customthe solvent was evaporated under reduced pressure
4. additionEthyl acetate was added to the residue
5. customthe insoluble material was separated by filtration
6. concentrationthe filtrate was concentrated
7. additionA mixture of the residue and 6N hydrochloric acid (0.5 mL) in acetonitrile (5 mL)
8. stirringwas stirred at room temperature for 1 hr
9. additionTo the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution
10. extractionthe mixture was extracted with ethyl acetate
11. customThe organic layer was separated
12. washwashed with water and saturated brine
13. dry with materialdried over anhydrous sodium sulfate
14. customthe solvent was evaporated under reduced pressure
15. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-3bfd861b87a34d849b274b52e001c5a5

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822699B2