Hydrochloric Acid → Nepsilon-(2-hydroxy-3-dodecyloxypropyl)-L-lysine hydrochloride

HRID 619006

Reaction equation

HRID 619006 reaction equation
[ClH:1].[NH2:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].[OH-].[Na+].[CH2:14]([O:26][CH2:27][CH:28]1[O:30][CH2:29]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].Cl>O.C(O)(C)C>[ClH:1].[OH:30][CH:28]([CH2:27][O:26][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:29][NH:8][CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]([C:9]([OH:11])=[O:10])[NH2:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 171631-Dodecyl glycidyl ether2×HCID 69568L-Lysine monohydrochloride

Product 1

HCID 18392215Nepsilon-(2-hydroxy-3-dodecyloxypropyl)-L-lysine hydrochlorideYield 23.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

L-lysine hydrochloride (18.3 g, 0.1 mols) and 2.0 g (0.2 mols) of sodium hydroxide were dissolved in 100 ml of water in a three-necked round flask, and 100 ml of i-propanol were added thereto. Then, 24.2 g (0.1 mols) of dodecylglycidyl ether were added dropwise thereto over a period of 30 minutes while being heat-refluxed and stirred. Further, the mixture was stirred under reflux for 3 hours. It was identified through TLC and gas chromatography that dodecylglycidyl ether disappeared. Thereafter, the resulting mixture was neutralized with 10.1 g (0.1 mols) of 36% hydrochloric acid. The reaction solution was concentrated under reduced pressure, and the residue was purified through silica-gel column chromatography (Kieselgel 60, eluent=mixture of chloroform, methanol and acetic acid at a ratio of 3:1:0.5) to give 10.1 g of Nε-(2-hydroxy-3-dodecyloxypropyl)-L-lysine hydrochloride (yield 23.7%).

Workup

  1. temperatureover a period of 30 minutes while being heat-refluxed
  2. stirringFurther, the mixture was stirred
  3. temperatureunder reflux for 3 hours
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. customthe residue was purified through silica-gel column chromatography (
  6. additionKieselgel 60, eluent=mixture of chloroform, methanol and acetic acid at a ratio of 3:1:0.5)

Sources & evidence

ORD record
ord-fe2bd8fdb39448feae7b8349a917d6a3
Source dataset
uspto-grants-1999_09
Patent number
US05958869

Linked notes

Loading…