Water → HCID 86759009, compound

HRID 1369050Notes

Reaction equation

HRID 1369050 reaction equation
[C:1](O)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:21][C@H:22]([C:27]([OH:29])=[O:28])[CH2:23][CH2:24][CH2:25][NH2:26].O>C1(C)C(C)=CC=CC=1>[CH2:1]([NH:26][CH2:25][CH2:24][CH2:23][C@@H:22]([C:27]([OH:29])=[O:28])[NH2:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 962WaterHCID 86759010HCID 86759010, compound

Product 1

HCID 86759009HCID 86759009, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

ornithine oleate (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 29.1 g of Nδ-oleyl ornithine (yield 86.9%). 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-f4c8fc4b539d486c8106ecfdfda72163
Source dataset
uspto-grants-2003_06
Patent number
US06576695B1

Reaction notes

Loading…