Hydrochloric Acid → HCID 54739191, compound

Participants

Reaction Steps

Ethyl-2-{cyclohexyl[3-(ethyloxy)-3-oxopropanoyl]hydrazono}-3,3-dimethylbutanoate. DBU (0.21 ml, 1.393 mmol) was added to a solution of the compound from example 99a) (0.323 g, 1.270 mmol) in Tetrahydrofuran (THF) (1 ml) at 0° C. The reaction was brought to room temperature and stirred for 10 minutes. The temperature was then reduced to 0° C. and ethyl malonyl chloride (0.19 ml, 1.410 mmol) was added. The reaction stirred for 2.5 h at room temperature followed by the addition of 1N HCl. The solution was diluted with H2O and EtOAc and the layers separated. The aqueous phase was backextracted with EtOAc several times. The combined organic layers were washed with Brine, dried (MgSO4), filtered and concentrated. The product was purified by column chromatography (SiO2, 5-25% EtOAc/Hexanes) to give a mixture of the title compound and the cyclized product 56c) (197 mg, 42%). LCMS (ES+) m/z 369.0, 323.0 (MH+).

Provenance & Evidence