Acetic Acid → (Z)-2-ethoxy-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]acrylic acid

Participants

Reaction Conditions

Reaction Steps

1.2 mL (1.2 mmol) of aqueous 1 M lithium hydroxide solution are added to a solution of 0.4 g (0.8 mmol) of ethyl (Z)-2-ethoxy-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]acrylate in 8 mL of tetrahydrofuran. The reaction mixture is stirred at 68° C. for 18 hours. After cooling, the reaction is worked up by addition of 1.2 mL (1.2 mmol) of aqueous 1 M acetic acid solution and 10 mL of water and extraction with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and then dried over magnesium sulfate. The solvents are evaporated off. The crude product obtained is purified by chromatography on a column of silica eluted with a 98/2 dichloromethane/methanol mixture to give 240 mg (68%) of (Z)-2-ethoxy-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]acrylic acid in the form of a colorless oil.

Provenance & Evidence