Water → N6-Capryloyl lysine

HRID 1369049Notes

Reaction equation

HRID 1369049 reaction equation
[C:1]([OH:10])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[NH2:11][C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17].O>C1(C)C(C)=CC=CC=1>[C:1]([NH:17][CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]([C:18]([OH:20])=[O:19])[NH2:11])(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 962WaterHCID 86756040Lysine octanoate

Product 1

HCID 90242N6-Capryloyl lysineYield 81.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Lysine octanoate (35.0 g) was suspended in 300 ml of xylene using a 600-milliliter reaction vessel. The suspension was boiled through heating, and water formed through azeotropic distillation was removed outside the system. After it was identified that a stoichiometric amount of water was removed (reaction time 3 hours), the residue was cooled. Crystals precipitated were separated through filtration, and washed with 100 ml of a 50% ethanol solution. The crystals were recrystallized from a sulfuric acid aqueous solution to obtain 26.9 g of Nε-octanoyl lysine (yield 81.9%). This is designated Derivative B.

Workup

  1. customa 600-milliliter reaction vessel
  2. temperaturethrough heating
  3. customwas removed outside the system
  4. customwas removed
  5. custom(reaction time 3 hours)
  6. temperaturethe residue was cooled
  7. customCrystals precipitated
  8. customwere separated through filtration
  9. washwashed with 100 ml of a 50% ethanol solution
  10. customThe crystals were recrystallized from a sulfuric acid aqueous solution

Sources & evidence

ORD record
ord-3c6ec3de2c4e4ef5804df380539e7039
Source dataset
uspto-grants-2003_06
Patent number
US06576695B1

Reaction notes

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