2,3-Bis[(9Z)-9-octadecen-1-yloxy]-1-propanol → 3-O-(2-dimethylaminoethyl)sulfamoyl-1,2-O-dioleylglycerol

HRID 376425

Reaktionsgleichung

Reaktionsgleichung von HRID 376425
[CH2:1]([O:19][CH2:20][CH:21]([CH2:41][OH:42])[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:43][N:44]([CH3:52])[CH2:45][CH2:46][NH:47][S:48](Cl)(=[O:50])=[O:49]>C(Cl)Cl.N1C=CC=CC=1.C(Cl)Cl>[CH3:43][N:44]([CH3:52])[CH2:45][CH2:46][NH:47][S:48]([O:42][CH2:41][CH:21]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:20][O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:50])=[O:49]

Komponenten

5

Edukt 2

HCID 53803432,3-Bis[(9Z)-9-octadecen-1-yloxy]-1-propanolHCID 19361100(2-Dimethylaminoethyl)sulfamoyl chloride

Produkt 1

HCID 867518623-O-(2-dimethylaminoethyl)sulfamoyl-1,2-O-dioleylglycerolAusbeute 18,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21875418Pyridine methylene chlorideLösungsmittel

Versuchsvorschrift

In 4 ml of methylene chloride-pyridine (2:1) was dissolved 150 mg (0.25 mmol) of 1,2-O-dioleylglycerol. Then, 1 ml of a solution of 150 mg (0.75 mmol) (2-dimethylaminoethyl)sulfamoyl chloride in methylene chloride was added and the reaction was carried out at ambient temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was treated with methylene chloride-saturated aqueous sodium hydrogen carbonate solution. The methylene chloride layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography (silica gel/methylene chloride-methanol) to provide 34 mg (18%) of the title compound of the invention.

Aufarbeitung

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionthe residue was treated with methylene chloride-saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialThe methylene chloride layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-88f5d475501241098154bbe215df8e61
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020317

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