1-Hydroxybenzotriazole → HCID 6482306, compound

Participants

Reaction Conditions

Reaction Steps

(S)-N-[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl amine (0.100 gm, 0.00034 moles) was taken up in 1:1 THF-water mixture (20 ml). To this was added 4-(4-chlorophenyl)-4-oxobutanoic acid (0.072 g, 0.00034 moles and HOBt (0.046 g, 0.00034 moles). The resulting mixture was cooled to 0° C., and then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.071 gm, 0.00037 moles) was added. The resulting mixture was allowed to warm to room temperature and then stirred for 24 hr. The reaction mixture was concentrated and 2 ml of saturated aqueous sodium bicarbonate solution was added, stirred for 15 min and then extracted with dichloromethane. The organic layer was separated and evaporated off. The residue was chromatographed over silica gel (100-200 mesh, 20 g) and eluted with mixture of ethyl acetate:hexane, and finally with ethyl acetate. The combined fractions were concentrated to give (0.070 gm, 42%) of the title compound as a white solid.

Provenance & Evidence