Dimethylformamide → 2-O-(3-diethylaminopropionyl)-1,3-O-dioleoylglycerol

HRID 724773Notes

Reaction equation

HRID 724773 reaction equation
CN(C)C=O.[C:6]([O:25][CH2:26][CH:27]([CH2:29][O:30][C:31](=[O:49])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]/[CH:39]=[CH:40]\[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[OH:28])(=[O:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[CH2:50]([N:52]([CH2:58][CH3:59])[CH2:53][CH2:54][C:55](O)=[O:56])[CH3:51]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:50]([N:52]([CH2:58][CH3:59])[CH2:53][CH2:54][C:55]([O:28][CH:27]([CH2:29][O:30][C:31](=[O:49])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]/[CH:39]=[CH:40]\[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:26][O:25][C:6](=[O:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:56])[CH3:51]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 247454N,N-Diethyl-beta-alanineHCID 54971651,3-Diolein

Product 1

HCID 111817842-O-(3-diethylaminopropionyl)-1,3-O-dioleoylglycerolYield 62.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a solvent mixture of 3 ml N,N-dimethylformamide and 6 ml methylene chloride was dissolved 172 mg (0.277 mmol) of 1,3-dioleoylglycerol followed by addition of 101 mg (0.556 mmol) of N,N-diethyl-β-alanine (hydrochloride), 114 mg (0.553 mmol) of N,N-dicyclohexylcarbodiimide, and 7 mg (0.057 mmol) of 4-dimethylaminopyridine and the mixture was stirred overnight. This reaction mixture was then filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in methylene chloride and washed with water. The washed solution was dried and concentrated and the residue was subjected to column chromatography (silica gel/methylene chloride-methanol) to provide 129 mg (62%) of the title compound.

Workup

  1. filtrationThis reaction mixture was then filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed with water
  5. customThe washed solution was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-63c8be7648da45d9bde169d072ff3481
Source dataset
uspto-grants-1998_01
Patent number
US05705188

Reaction notes

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