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

HRID 968091Notes

Reaction equation

HRID 968091 reaction equation
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]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 69568L-Lysine monohydrochlorideHCID 45040426HCID 45040426, compoundHCID 86595252Water acetone triethylamine

Product 1

HCID 86595251Nepsilon-(z-15-tetracosenoyl)-L-lysine

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

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.

Workup

  1. additionwas added in order
  2. customfrom precipitating as a thick voluminous mass
  3. waitwas continued for an additional hour
  4. temperaturev/v) to pH 4 and chilled
  5. customThe light foamy product was separated by filtration
  6. washwashed with water and hot dioxane

Sources & evidence

ORD record
ord-fb340162a160414eb11a095486a7e12a
Source dataset
uspto-grants-2005_10
Patent number
US06956059B2

Reaction notes

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