Potassium Phosphate, Tribasic → [(6-{(4S)-4-[(tert-Butoxycarbonyl)amino]-2-oxopyrrolidin-1-yl}-2-nitropyridin-3-yl)oxy]acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of [(3S)-5-oxopyrrolidin-3-yl]carbamic acid tert-butyl ester (synthesized with reference to WO2004/22536; 505 mg, 2.52 mmol), [(6-bromo-2-nitropyridin-3-yl)oxy]acetic acid ethyl ester (synthesized with reference to WO2004/2992; 769 mg, 2.52 mmol), palladium acetate (56.6 mg, 0.252 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (157 mg, 0.252 mmol), potassium phosphate (1.74 g, 7.56 mmol) and 1,4-dioxane (25 ml) was stirred under a stream of nitrogen gas at 100° C. for 6 hours. After cooling, ethyl acetate was added to the reaction solution to remove the insoluble material by filtration. The obtained filtrate was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 380 mg (36%) of the title compound in the form of a light brown syrup.

Provenance & Evidence