Triethylamine → HCID 22262241, compound

Participants

Reaction Steps

To a solution of ethyl (2RS,3RS)-3-(3-chlorophenyl)-2-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-3-hydroxypropionate (11.44 g, 29.4 mmol) in tetrahydrofuran-ethanol (60 ml-60 ml) was added 1N sodium hydroxide (60 ml, 60 mmol) at room temperature, and the mixture was stirred overnight at room temperature. After completion of the reaction, the organic solvent was evaporated under reduced pressure. The aqueous layer was acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and concentrated under reduced pressure to give a colorless transparent oil. To a solution of the oil in tetrahydrofuran (300 ml) were added triethylamine (6.2 ml, 44.1 mmol) and diphenylphosphoryl azide (7.6 ml, 35.3 mmol), and the mixture was heated under reflux for 4 hrs. The solvent was evaporated, and the residue was diluted with ethyl acetate and washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give (4RS,5SR)-5-(3-chlorophenyl)-4-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-1,3-oxazolidin-2-one (8.11 g, 77%) as colorless crystals.

Provenance & Evidence