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

HRID 728239Notes

Reaction equation

HRID 728239 reaction equation
[C:1]([OH:18])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl.[NH2:20][C@H:21]([C:27]([OH:29])=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26].C(N(CC)CC)C.C(O)(=O)C>CC(C)=O.O>[O:18]=[C:1]([NH:26][CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]([C:27]([OH:29])=[O:28])[NH2:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 985Palmitic AcidHCID 8471TriethylamineHCID 69568L-Lysine monohydrochloride

Product 1

HCID 100425N6-(1-Oxohexadecyl)-L-lysineYield 73%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

Following the procedure of A. Paquet Can. J. Chem. 54, 733 (1976), 353 mg. (1 mmol) of the succinimidylester of hexadecanoic acid, prepared as in example 2, was suspended in 2 ml acetone and added to a solution of 183 mg (1 mmol) L-lysine hydrochloride and 0.27 ml (ca. 2 mmol) triethylamine in 2 ml water. The reaction mixture was stirred vigorously for at least 4 h, then neutralized with acetic acid and diluted with water. The precipitate was removed by filtration and washed with water, methanol and ether. Repeated crystallizations from acetic acid/water and acetic acid gave 280 mg (73%) colourless crystals, m.p. 240°-245° C. (reported 210°-220° C.)

Workup

  1. customThe precipitate was removed by filtration
  2. washwashed with water, methanol and ether
  3. customcrystallizations from acetic acid/water and acetic acid

Sources & evidence

ORD record
ord-412eac3935a74c7f8adb0d2fa1c6d42c
Source dataset
uspto-grants-1991_09
Patent number
US05047535

Reaction notes

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