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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence