Hydrochloric Acid → N-(2-hydroxy-3-dodecyloxy)propyl-L-arginine hydrochloride

HRID 580783

Reaction equation

HRID 580783 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[CH:13]([OH:16])(C)[CH3:14].[CH2:17]([O:29][CH2:30][CH:31]1O[CH2:32]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]CC.[ClH:34]>O>[ClH:34].[OH:16][CH:13]([CH:17]([O:29][CH2:30][CH2:31][CH2:32][NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 171631-Dodecyl glycidyl ether2×HCID 178418600HCID 178418600, compound

Product 1

HCID 178443432N-(2-hydroxy-3-dodecyloxy)propyl-L-arginine hydrochlorideYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

L-arginine (17.4 g, 0.1 mols) was 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 (made by Sakamoto Yakuhin Kogyo Co., Ltd.) 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 determined 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 made by Merck & Co., Inc., eluent=mixture of chloroform, methanol and acetic acid at a ratio of 3:1:0.5) to give 15.0 g of N-(2-hydroxy-3-dodecyloxy)propyl-L-arginine hydrochloride (yield 36.0%).

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 (Kieselgel 60
  6. addition, eluent=mixture of chloroform, methanol and acetic acid at a ratio of 3:1:0.5)

Sources & evidence

ORD record
ord-686539c3e530471ea9f28bac0c5cbb0e
Source dataset
uspto-grants-1999_07
Patent number
US05919748

Linked notes

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