Glutaric Acid → HCID 10587290, compound

Participants

Reaction Steps

The CPVK3 was synthesized referring to a document (Salmon-Chemin L., Buisine E., Yardley V., Kohler S., Debreu M. A., Landry V., Sergheraert C., Croft S. L., Krauth-Siegel R. L., and Davioud-Charvet E., J. Med. Chem., 2001, 44, 548-565). 2-methyl-1,4-naphthoquinone, glutaric acid, and AgNO3 were suspended in a 30% aqueous CH3CN solution, heated, and stirred to dissolve completely. Then, a 30% aqueous CH3CN solution of (NH4)2S2O8 was added dropwise in 60 minutes. After completing the dropwise addition, the mixture was stirred at 65° C. for 5 minutes as it was. Cooling of the reaction mixture to room temperature resulted in precipitation of a yellow brown solid. Water and ethyl acetate were added to the reaction mixture, and an organic layer was washed with water using a separating funnel. Further, the organic layer was washed with water. A 2N-aqueous solution of sodium bicarbonate was added to the organic layer, and a sodium salt of a target compound was extracted to an aqueous layer. Then, the aqueous layer was adjusted to a pH of 2 or less using 37% hydrochloric acid, and a precipitated solid was collected by filtration. The solid was sufficiently washed with cool water, and dried under reduced pressure, to thereby obtain a yellow brown powder 2-(3-carboxypropyl)-3-methyl-1,4-naphthoquinone.

Provenance & Evidence