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

HRID 580786

Reaction equation

HRID 580786 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:32][CH2:33][CH:34]1O[CH2:35]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]CC.Cl.[CH:38]([OH:41])(C)[CH3:39]>O>[ClH:1].[OH:41][CH:38]([CH:14]([O:32][CH2:33][CH2:34][CH2:35][NH:8][CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]([C:9]([OH:11])=[O:10])[NH2:2])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:39]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 61831Oxirane, 2-[(octadecyloxy)methyl]-2×HCID 69568L-Lysine monohydrochloride

Product 1

HCID 21309926Nepsilon-(2-hydroxy-3-octadecyloxy)propyl-L-lysine hydrochlorideYield 23.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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, 32.6 g (0.1 mols) of octadecylglycidyl 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 octadecylglycidyl 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 12.0 g of Nε-(2-hydroxy-3-octadecyloxy)propyl-L-lysine hydrochloride (yield 23.6%).

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-5c24d0738e85486587a0d550a5fec87a
Source dataset
uspto-grants-1999_07
Patent number
US05919748

Linked notes

Loading…