Acetic Acid → N6-(1-Oxohexadecyl)-L-lysine

HRID 1704288Notes

Reaction equation

HRID 1704288 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].C(N(CC)CC)C.[C:18](ON1C(=O)CCC1=O)(=[O:34])[CH2:19][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][CH3:33].C(O)(=O)C>O>[C:18]([NH:7][CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]([C:8]([OH:10])=[O:9])[NH2:1])(=[O:34])[CH2:19][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][CH3:33]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5962L-LysineHCID 8471TriethylamineHCID 4620598Palmitic acid N-hydroxysuccinimide

Product 1

HCID 100425N6-(1-Oxohexadecyl)-L-lysineYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the solution of L-lysine (1 mmol) in water (2 ml) and triethylamine (0.27 ml, 2 mmol) 1 mmol of succinimidyl palmitate (suspended in 2 ml of acetone) was added at room temperature under stirring. Stirring of the reaction mixture was continued for 4h. Triethylamine was removed under reduced pressure, the precipitate was collected by filtration, washed with water and ethanol, crystallized from glacial acetic acid giving an 86% yield of the title compound. Analysis data are given in Table 2.

Workup

  1. stirringStirring of the reaction mixture
  2. customTriethylamine was removed under reduced pressure
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water and ethanol

Sources & evidence

ORD record
ord-e5237ac844f14b98bc5496c6a6836a6c
Source dataset
uspto-grants-1978_11
Patent number
US04126628

Reaction notes

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