Hydrochloric Acid → HCID 178443282, compound

HRID 1739607Notes

Reaction equation

HRID 1739607 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)CC.[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:20][CH:18]([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])[CH2:19][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 10311-PropanolHCID 171631-Dodecyl glycidyl ether2×HCID 178418600HCID 178418600, compound

Product 1

HCID 178443282HCID 178443282, compoundYield 33,108.199%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

L-arginine (17.4 g, 0.1 mmols) were dissolved in 100 ml of water in a three-necked round flask, and 100 ml of propanol were added thereto. Dodecyl glycidyl ether [made by Sakamoto Yakuhin Kogyo Co., Ltd., 24.2 g (0.1 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 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-dodecyloxypropyl)-L-arginine hydrochloride in a yield of 36.0%.

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

Sources & evidence

ORD record
ord-aa430d77e06d4ea8a5ccfdcac44f17c2
Source dataset
uspto-grants-1999_10
Patent number
US05968492

Reaction notes

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