Triethylamine → Nepsilon-(z-15-tetracosenoyl)-L-lysine

Participants

Reaction Steps

To a vigorously-stirred solution of L-lysine monohydrochloride (13 mmol, 2.4 g, commercially available) and triethylamine (39 mmol, 3.9 g) in 50 mL of water-acetone (1:1), was added succinimidyl nervonate (13 mmol, 6.0 g, prepared as in Example 1A) in portions during 0.5 h. During the addition, more water-acetone-triethylamine (10:10:2) was added in order to prevent the product from precipitating as a thick voluminous mass. Stirring was continued for an additional hour. The mixture was then acidified with hydrochloric acid in water (1:1, v/v) to pH 4 and chilled. The light foamy product was separated by filtration and washed with water and hot dioxane to yield the title compound.

Provenance & Evidence