Triethylamine → HCID 54139884, compound

Participants

Reaction Steps

To a stirred solution of L-phenylalanine methyl ester HCl (2.0 mmol, 431 mg) in absolute ethanol (20 mL) was added triethylamine (2.2 mmol, 202 mg; 278 μL) and the resulting solution was stirred at room temperature for 15 minutes. Subsequently, neat 3,4-diethoxy-3-cyclobutene-1,2-dione (2 mmol, 340 mg; 296 μL) was added dropwise and the resulting solution was stirred at room temperature overnight, during which a white solid precipitated out of solution. The volatiles were removed in vacuo and the residue was taken up in EtOAc and partitioned between EtOAc and water. The organics were dried (Na2SO4) and purified by flash chromatography (SiO2 :1) 20% EtOAc/hexane; 2) 30% EtOAc/hexane; 3) 40% EtOAc/hexane) to afford the title compound as a colorless oil (551 mg; 85%).

Provenance & Evidence