Acetic Acid → HCID 10766040, compound

Participants

Reaction Steps

1-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (4 g) was dissolved in 30 ml of 1-methyl-2-pyrrolidone, to which 60% sodium hydride in oil (0.55 g) was added. The mixture was vigorously stirred at room temperature for 30 minutes and then added to a solution of 5.2 g of benzyl (2S)-2-trifluoromethanesulfonyloxypropionate (prepared in Example 3) in 80 ml of tetrahydrofuran under nitrogen atmosphere at -40° to -50° C. over the period of 10 minutes. The mixture was stirred at -20° to -40° C. for 50 minutes, followed by addition of 9.6 ml of acetic acid. Then, the reaction solution was diluted with 100 ml of ethyl acetate, washed with 50 ml of water, 1N-hydrochloric acid (50 ml×2) and 50 ml of an aqueous solution of sodium chloride successively, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (silica gel: 200 g, eluent; hexane:ethyl acetate=2:3) to give 5.3 g of benzyl (2R)-2-[3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2,3-dihydro-2-oxo-1H-imidazol-1-yl]propionate (yield: 85%) as colorless powdery crystals.

Provenance & Evidence