Water → 2-[4-(2-Carboxyethyl)phenyl]-4-(3-heptyl-1-methylureido)pyridinium acetate

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Reaction Steps

100 mg (2.5 mmol, 4 eq) of sodium hydroxide are added to a solution of 260 mg (0.61 mmol, 1 eq) of ethyl 3-{4-[4-(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 crystallized from pentane. 143 mg of 2-[4-(2-carboxyethyl)phenyl]-4-(3-heptyl-1-methylureido)pyridinium acetate are obtained. Yield=59%. m.p.=71-73° C.

Provenance & Evidence