N,N'-Dimethylethylenediamine → 4-(5-Methyl-2-oxooxazolidin-3-yl)benzoic acid

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Reaction Steps

A mixture of 1-amino-2-propanol (1.4 g), diethyl carbonate (2.4 mL) and potassium carbonate (500 mg) was stirred at 150° C. for 3 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated to give 5-methyloxazolidin-2-one (1.9 g). To a mixture of ethyl 4-iodobenzoate (3.2 mL), 5-methyloxazolidin-2-one (1.9 g), potassium carbonate (8 g) and copper (I) iodide (720 mg) were added toluene (20 mL) and N,N′-dimethylethylenediamine (800 μL), and the mixture was refluxed for 3 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was dissolved in methanol (20 mL) and 1,4-dioxane (20 mL), 1N aqueous sodium hydroxide solution (40 mL) was added, and the mixture was stirred at room temperature for 3 hr. 1N hydrochloric acid (40 mL) was added, and the mixture was extracted with chloroform. The solvent was evaporated to give the title compound (3.9 g).

Provenance & Evidence