Water → N6-Capryloyl lysine

HRID 1704289Notes

Reaction equation

HRID 1704289 reaction equation
Cl.[NH2:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].O.C(N(CC)CC)C.[C:20](ON1C(=O)CCC1=O)(=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CC(C)=O>[C:20]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]([C:9]([OH:11])=[O:10])[NH2:2])(=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 69568L-Lysine monohydrochlorideHCID 35427742,5-Dioxopyrrolidin-1-YL octanoate

Product 1

HCID 90242N6-Capryloyl lysineYield 97.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of L-lysine monohydrochloride (1.66 g, 9.1 mmol) in 16 of water, 16 ml of acetone and 3.83 ml (27.3 mmol) of triethylamine, succinimidyl caprylate (2.21 g, 9.1 mmol) was added portion-wise under stirring at room temperature within the period of 1h. Stirring was continued for 3h. The organic solvent was removed in vacuo and the reaction mixture was neutralized using diluted hydrochloric acid and allowed to stand at 0° overnight. The white precipitate was collected by filtration, washed with cold water, dried yielding 2.41 g (97%) of the crude product. Infrared spectrum exhibited typical pattern of ε-N-mono-substituted lysine derivative: 1580-1590 cm-1 (ionized carboxyl group), 1635 and 1520-1535 (amide bands). The compound was further purified by washing with ethanol and crystallizing from glacial acetic acid giving 2.08 g (84%) of the pure title compound.

Workup

  1. stirringStirring
  2. waitwas continued for 3h
  3. customThe organic solvent was removed in vacuo
  4. waitto stand at 0° overnight
  5. filtrationThe white precipitate was collected by filtration
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-bd8e1cbc3078479d81d9a9c65268b2d2
Source dataset
uspto-grants-1978_11
Patent number
US04126628

Reaction notes

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