Methyl iodide → HCID 91019241, compound

Participants

Reaction Steps

A solution containing 1 equivalent of (3EZ,5S)-1-([1,1′-biphenyl]-4-ylcarbonyl)-5-[5-(1-piperazinylmethyl)-1,2,4-oxadiazol-3-yl]-3-pyrrolidinone O-methyloxime (Example 48), dissolved in dry DCM at 0° C. in presence of 1.5 equivalent of triethyl amine, was reacted with 1 equivalent of methyl iodide. The reaction mixture was stirred at room temperature for 12 hours. The reaction was hydrolyzed and then made basic with sodium carbonate solution (10%) and extracted with DCM. The organic phase was then dried with magnesium sulfate, and concentrated in vacuo to give a residue which was purified by flash-chromatography using dichloromethane/methanol as eluent to give the expected product, (3EZ,5S)-1-([1,1′-biphenyl]-4-ylcarbonyl)-5-{5-[(4-methyl-1-piperazinyl)methyl]-1,2,4-oxadiazol-3-yl}-3-pyrrolidinone O-methyloxime, as a mixture of E-/Z-isomers, in 50% yield (99.9% purity by HPLC). The pure Z-isomer could be separated by flash-chromatography, and was obtained in 31% yield (98.9% purity by HPLC).

Provenance & Evidence