Dicyclohexylcarbodiimide → 3-O-(4-dimethylaminobutanoyl)-1,2-O-dioleylglycerol

HRID 376423

Reaction equation

HRID 376423 reaction equation
[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].Cl.[CH3:44][N:45]([CH3:52])[CH2:46][CH2:47][CH2:48][C:49](O)=[O:50].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C=O.CN(C)C1C=CN=CC=1>[CH3:44][N:45]([CH3:52])[CH2:46][CH2:47][CH2:48][C:49]([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]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 53803432,3-Bis[(9Z)-9-octadecen-1-yloxy]-1-propanolHCID 126916404-(Dimethylamino)butyric acid hydrochloride

Product 1

HCID 867518603-O-(4-dimethylaminobutanoyl)-1,2-O-dioleylglycerolYield 87.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

In 6 ml of methylene chloride-N,N-dimethylformamide (1:2) was dissolved 120 mg (0.20 mmol) of 1,2-O-dioleylglycerol, followed by addition of 168 mg (1 mmol) of 4-dimethylaminobutyric acid hydrochloride. Then, 206 mg (1 mmol) of N,N'-dicyclohexylcarbodiimide (DCC) and 25 mg (0.2 mmol) of 4-dimethylaminopyridine were further added and the reaction was conducted at ambient temperature overnight. The precipitated byproduct urea was filtered off using a glass filter and the filtrate was concentrated to dryness under reduced pressure and treated with methylene chloride-saturated aqueous sodium hydrogen carbonate solution. After phase separation, the methylene chloride layer was dried over sodium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to column chromatography (silica gel/methylene chloride-methanol) to provide 123 mg (87%) of the title compound of the invention.

Workup

  1. filtrationThe precipitated byproduct urea was filtered off
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated to dryness under reduced pressure
  4. additiontreated with methylene chloride-saturated aqueous sodium hydrogen carbonate solution
  5. customAfter phase separation
  6. dry with materialthe methylene chloride layer was dried over sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c3e2d99100fc40ccb67ccb4087237832
Source dataset
uspto-grants-2000_02
Patent number
US06020317

Linked notes

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