Water → N6-(1-Oxooctadecyl)-L-lysine

HRID 1369048Notes

Reaction equation

HRID 1369048 reaction equation
[C:1]([OH:20])(=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][CH2:16][CH2:17][CH3:18].[NH2:21][C@H:22]([C:28]([OH:30])=[O:29])[CH2:23][CH2:24][CH2:25][CH2:26][NH2:27].O>C1(C)C(C)=CC=CC=1>[C:1]([NH:27][CH2:26][CH2:25][CH2:24][CH2:23][C@@H:22]([C:28]([OH:30])=[O:29])[NH2:21])(=[O: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][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 962WaterHCID 86756039HCID 86756039, compound

Product 1

HCID 104260N6-(1-Oxooctadecyl)-L-lysineYield 85.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Lysine stearate (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 28.8 g of Nε-stearoyl lysine (yield 85.9%). This is designated Derivative A.

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-fa2e5096620149b7bcf05366c96b9b7f
Source dataset
uspto-grants-2003_06
Patent number
US06576695B1

Reaction notes

Loading…