Potassium Phosphate, Tribasic → 5-((4-iodo-1H-pyrazol-1-yl)methyl)oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium phosphate tribasic (6.57 g, 30.9 mmol), 4-iodo pyrazole (2.00 g, 10.3 mmol), and 5-(chloromethyl)-1,3-oxazolidin-2-one (2.80 g, 20.6 mmol) in 1,4-dioxane (103 mL) was sealed in a pressure vessel and heated for 72 hours at 110° C. Upon cooling to room temperature, the mixture was diluted with water and dichloromethane. The organic layer was separated, washed with water, and concentrated under reduced pressure. The residue was triturated with a mixture of methanol and hexanes for several hours at room temperature, and then the precipitate was collected by filtration to afford 5-[(4-iodo-1H-pyrazol-1-yl)methyl]-1,3-oxazolidin-2-one. MS ESI calc'd. for C2H8IN3O2 [M+H]+ 294. found 294. The enantiomers were separated by chiral SFC (supercritical fluid chromatography), IC column with 20% isopropyl alcohol in CO2 to give isomer 1 (faster eluting) and isomer 2 (slower eluting).

Provenance & Evidence