Hydrochloric Acid → HCID 54739192, compound

Participants

Reaction Steps

Ethyl-2-{cyclohexyl[3-(ethyloxy)-3-oxopropanoyl]hydrazono}-3-methylbutanoate. DBU (0.35 ml, 2.322 mmol) was added to a solution of the compound from example 98a) (0.51 g, 2.122 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 (0.32 ml, 2.374 mmol) was added. The reaction was brought to room temperature and stirred for 2.5 h. 1N HCl was added and the solution diluted with H2O and EtOAc. The layers were separated and aqueous phase 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, 10-25% EtOAc/Hexanes) to give a mixture of the title compound and the cyclized product 55c) (126 mg, 13%). LCMS (ES+) m/z 355.2, 309.2 (MH+).

Provenance & Evidence