Ethylenediaminetetraacetic Acid → HCID 66858320, compound

Participants

Reaction Conditions

Reaction Steps

Step N (1): Followed the method of R. Roy et. al Tetrahedron 2007, 63, 4912. To a solution of N-(2-methoxy-4-nitrophenyl)formamide (4.0 g, 28 mmol, U. Mario et. al General Pharmacology, 1979, 10, 309) and N-formylglycine ethyl ester (16.6 g, 153 mmol) in dichloromethane (20 mL) were added triethylamine (28 mL, 72 mmol) and POCl3 (8.0 mL, 200 mmol) dropwise at 0° C. The reaction was stirred at 0° C. for 2 h. The mixture was filtered over silica using dichloromethane/diethyl ether (4/1) and concentrated under reduced pressure. The crude residue was dissolved in THF (100 mL) to which Cu2O (400 mg, 2.8 mmol) and L-proline (644 mg, 5.6 mmol) were added and the resulting solution stirred at rt for 4 h. A solution of aq EDTA (5%) was added to the reaction mixture, which was then extracted with EtOAc. The crude residue was purified using silica gel column chromatography (EtOAc/dichloromethane) to afford ethyl 1-(2-methoxy-4-nitrophenyl)-1H-imidazole-4-carboxylate (2.0 g, 24% yield).

Provenance & Evidence