Benzyl Alcohol → [5-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-yl]carbamic acid benzyl ester

Participants

Reaction Steps

A mixture of 5-oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-carboxylic acid (764 mg, 2.76 mmol), diphenyl phosphoryl azide (0.891 ml, 4.13 mmol), triethylamine (0.626 ml, 4.49 mmol) and benzene (35 ml) was heated under reflux for 3 hours. Benzyl alcohol (21 ml) was added to the reaction solution, which was further heated under reflux overnight. After cooling, the insoluble material was removed by filtration, the filtrate was diluted with ethyl acetate, washed with a saturated sodium hydrogen carbonate aqueous solution 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 and chloroform/methanol) to yield 496 mg (47%) of the title compound in the form of a light yellow solid.

Provenance & Evidence