epsilon-(Benzyloxycarbonyl)-L-lysine → Nalpha-(3-hexadecanoyloxyoctadecanoyl)-Nepsilon-benzyloxycarbonyl-L-lysine

Participants

Reaction Steps

To a solution of N-hydroxysuccinimide ester of 3-hexadecanoyloxyoctadecanoic acid (7.5 g) prepared by the method of Example 8 (1) in dimethylformamide (200 ml) was added a solution of Nε -benzyloxycarbonyl-L-lysine (6.6 g) in 1N sodium hydroxide (23.6 ml) at room temperature. The mixture was stirred at ambient temperature for 3 hours. The precipitated solid was collected by filtration and the filtrate was concentrated under reduced pressure. The solid and the residue was combined. Then, the mixture was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water. The ethyl acetate solution was dried over magnesium sulfate, and then concentrated to give a residue which was dried up by high vacuum pump to afford powder of Nα -(3-hexadecanoyloxyoctadecanoyl)-Nε -benzyloxycarbonyl-L-lysine (8.5 g).

Provenance & Evidence