Diisopropylcarbodiimide → HCID 63383281, compound

Participants

Reaction Steps

Ethyl aminohydroxyiminoacetate (3.78 mmol, 0.5 g), 3-isoxazolecarboxylic acid (3.78 mmol, 0.428 g) and 1,3-diisopropylcarbodiimide (4.16 mmol, 0.525 g) were dissolved in DCM (70 ml) under nitrogen atmosphere. The mixture was stirred at RT for a day. The solvent was evaporated to dryness and the residue was dissolved in pyridine and refluxed for 6 h and overnight at RT. Pyridine was evaporated and the residue was diluted with DCM and water. The aqueous phase was extracted four times with DCM. The combined organics were washed with aqueous HCl solution, saturated NaHCO3, water and brine. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.396 g of the title compound was obtained. Rotamers were obtained in 1H-NMR and analysis was repeated at elevated temperature. 1H-NMR (400 MHz, DMSO-d6, +60° C.): δ 1.38 (t, 3H), 4.49 (q, 2H), 7.21 (d, 1H), 9.05 (d, 1H).

Provenance & Evidence