Cl.[NH2:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].C(N(CC)CC)C.[C:19](ON1C(=O)CCC1=O)(=[O:43])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].O.CC(C)=O.C(N(CC)CC)C>O.CC(C)=O>[C:19]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]([C:9]([OH:11])=[O:10])[NH2:2])(=[O:43])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]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.
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