Hydrochloric Acid → HCID 178443281, compound

HRID 1739608Notes

Reaction equation

HRID 1739608 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])([CH3:15])[CH3:14].[CH2:17]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:18]1[O:20][CH2:19]1.[ClH:34]>O>[ClH:34].[OH:16][CH:13]([CH2:15][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:14][N:1]([CH2:19][CH:18]([OH:20])[CH2:17][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[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 171631-Dodecyl glycidyl ether2×HCID 178418600HCID 178418600, compound

Product 1

HCID 178443281HCID 178443281, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

L-arginine (17.4 g, 0.1 mmols) was dissolved in 100 ml of water in a three-necked round flask, and 100 ml of i-propanol were added thereto. Dodecyl glycidyl ether (48.4 g, 0.2 mols) was added thereto dropwise over a period of 30 minutes while being heat-stirred under reflux, and the mixture was stirred as such under reflux for 3 hours. After it was identified through TLC and gas chromatography that dodecyl glycidyl ether disappeared, the residue 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 11.4 g of N,N-bis (2-hydroxy-3-dodecyloxypropyl)-L-arginine hydrochloride in a yield of 17.2%.

Workup

  1. temperatureunder reflux
  2. stirringthe mixture was stirred as such
  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, eluent
  6. additionmixture of chloroform, methanol and acetic acid at a ratio of 3:1:0.5)

Sources & evidence

ORD record
ord-70d7c1350f924ea19402d961cf1e8235
Source dataset
uspto-grants-1999_10
Patent number
US05968492

Reaction notes

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