Sodium Hydroxide → HCID 11718226, compound

Participants

Reaction Steps

170 mg (0.4 mmol) of ethyl 3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylate are dissolved in 5 ml of methanol. 50 mg of 10% palladium-on-charcoal are added. The reaction mixture is stirred for 3 hours at room temperature under a hydrogen atmosphere. The catalyst is filtered off and the solvents are then evaporated off and the oil obtained is used directly in the following reaction. 170 mg of sodium hydroxide are added to the solution of ethyl 3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoate in 5 ml of 9/1 tetrahydrofuran/methanol. The reaction mixture is stirred for two hours at room temperature. The reaction is stopped by adding 20 mL of water and 3 mL of acetic acid and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (7/3 to 1/1 heptane/EtOAc). 110 mg of 3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoic acid are obtained. Yield=69% over two steps. m.p.=108° C.

Provenance & Evidence