Acetic Acid → HCID 54739236, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 3-{2-[1-cyclohexyl-2-(ethyloxy)-2-oxoethylidene]hydrazino}-3-oxopropanoate. A solution of diethyl oxylate (4.1 mL, 30.0 mmol) in THF (50 mL) was cooled to −78° C. Cyclohexyl magnesium bromide (1.0M solution in THF, 36 mL, 36.0 mmol) was dropwise added and the solution stirred under a nitrogen atmosphere for 1.5 h at −78° C. The reaction was brought to 0° C. and quenched with 6N HCl. Et2O and H2O were added and the layers separated. The aqueous phase was backextracted with Et2O several times. The combined organic layers were washed with Brine, dried (MgSO4), filtered and concentrated. The resulting residue was dissolved in EtOH (20 mL) and partitioned between two microwave vials. Ethyl-3-hydrazino-3-oxopropionate (2.41 g, 18.0 mmol) and catalytic AcOH (0.2 mL, 3.50 mmol) were added to each vial. The reactions were heated in the microwave at 150° C. for 1 h. The reactions were cooled and combined in a round bottom flask. The solvent was removed under reduced pressure and the resulting residue was azeotroped with Toluene several times. The product was purified by column chromatography (SiO2, 10-30% EtOAc/Hexanes) to give the title compound (1.93 g, 21% over 2 steps). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.44-11.78 (m, 1H) 3.99-4.34 (m, 4H) 3.44-3.67 (m, 2H) 2.52-2.63 (m, 1H) 1.52-1.84 (m, 5H) 1.04-1.37 (m, 11H).

Provenance & Evidence