Dicyclohexylcarbodiimide → 1-Oleyl-3-palmitoylglycerol

HRID 2223432Notes

Reaction equation

HRID 2223432 reaction equation
[C:1]([O:18][CH2:19][CH:20]([CH2:22][OH:23])[OH:21])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.[C:48](O)(=O)[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]/[CH:56]=[CH:57]\[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65]>ClCCl>[CH2:48]([O:23][CH2:22][CH:20]([CH2:19][O:18][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[OH:21])[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]/[CH:56]=[CH:57]\[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 149001-MonopalmitinHCID 218852-DimethylaminopyridineHCID 445639Oleic Acid

Product 1

HCID 865944451-Oleyl-3-palmitoylglycerolYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Glycerol palmitate (example 2b) (5.516 g, 0.017 mol) was dissolved in dichloromethane (500 ml) and dicyclohexylcarbodiimide (5.165 g, 0.025 mol), dimethylaminopyridine (3.058 g, 0.025 mol) and oleic acid (4.714 g, 0.017 mol) were then added. The reaction mixture was stirred at room temperature for 24 hours. The dicyclohexylurea precipitate was filtered, washed with dichloromethane and the filtrate was evaporated under vacuum. The residue obtained was purified by silica gel chromatography (eluent:CH2Cl2) to give the desired compound as a white solid (yield: 23%).

Workup

  1. filtrationThe dicyclohexylurea precipitate was filtered
  2. washwashed with dichloromethane
  3. customthe filtrate was evaporated under vacuum
  4. customThe residue obtained
  5. customwas purified by silica gel chromatography (eluent:CH2Cl2)

Sources & evidence

ORD record
ord-71778fa577ee4f7a98175b4f6129d364
Source dataset
uspto-grants-2008_05
Patent number
US07375135B2

Reaction notes

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