Hydrochloric Acid → HCID 178442929, compound

HRID 619004Notes

Reaction equation

HRID 619004 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].C(O)(C)C.[CH2:17]([O:35][CH2:36][CH:37]1[O:39][CH2:38]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].[ClH:40]>O>[ClH:40].[OH:39][CH:37]([CH2:36][O:35][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][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:38][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]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 61831Oxirane, 2-[(octadecyloxy)methyl]-2×HCID 178418600HCID 178418600, compound

Product 1

HCID 178442929HCID 178442929, compoundYield 42.3%

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, 32.6 g (0.1 mols) of octadecylglycidyl 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 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 21.2 g of N-(2-hydroxy-3-octadecyloxypropyl)-L-arginine hydrochloride (yield 42.3%).

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-11c4b26d2b6f4837a096602a4293d9ca
Source dataset
uspto-grants-1999_09
Patent number
US05958869

Reaction notes

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