Réaction #158393

Équation de réaction

5-[4-(5-chloropent-1-yn-1-yl)-2-methoxyphenyl]-2-methyl-1,3-oxazole

ethyl N-(diphenylmethylene)glycinate

potassium carbonate

→

title compound

Rendement 58.9%

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

Rendement 58.9%

Solvants

ethyl acetate

acetonitrile

Conditions de réaction

Traitement

1. 1
   Lavagethe mixture was washed with water and saturated brine
2. 2
   Séchagedried over anhydrous sodium sulfate
3. 3
   Autrethe solvent was evaporated under reduced pressure
4. 4
   workup.ADDITIONEthyl acetate was added to the residue
5. 5
   Autrethe insoluble material was separated by filtration
6. 6
   Concentrationthe filtrate was concentrated
7. 7
   workup.ADDITIONA mixture of the residue and 6N hydrochloric acid (0.5 mL) in acetonitrile (5 mL)
8. 8
   workup.STIRRINGwas stirred at room temperature for 1 hr
9. 9
   workup.ADDITIONTo the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution
10. 10
    Extractionthe mixture was extracted with ethyl acetate
11. 11
    AutreThe organic layer was separated
12. 12
    Lavagewashed with water and saturated brine
13. 13
    Séchagedried over anhydrous sodium sulfate
14. 14
    Autrethe solvent was evaporated under reduced pressure
15. 15
    AutreThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Mode opératoire

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).

Source