N-[3-(methoxycarbonyl)-5-(octadecyloxy)phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester → N-(carboxymethyl)-N-[3-(methoxy-carbonyl)-5-(octadecyloxy)phenyl]glycine

Participants

Reaction Steps

A mixture of 2.63 g (3.67 mmol) of N-[3-(methoxycarbonyl)-5-(octadecyloxy)phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester and 0.5 g of 10% palladium on carbon in 150 ml of THF was shaken in a hydrogen atmosphere at room temperature for 3 hours. The catalyst was removed by filtration and the filtrate was concentrated to a solid which was recrystallized from methanol-water to give 1.84 g (93% yield, mp 119°-123°) of N-(carboxymethyl)-N-[3-(methoxy-carbonyl)-5-(octadecyloxy)phenyl]glycine.

Provenance & Evidence