Dicyclohexylcarbodiimide → 1-Oleyl-3-palmitoyl-2-tetradecylthioacetylglycerol

HRID 2223433Notes

Reaction equation

HRID 2223433 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([OH:41])[CH2:22][O:23][C:24](=[O:40])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[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].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.[CH2:66]([CH2:80][C:81](O)=[S:82])[CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH3:79]>ClCCl>[CH2:1]([O:19][CH:20]([C:81](=[S:82])[CH2:80][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH3:79])[CH:21]([CH2:22][O:23][C:24](=[O:40])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[OH:41])[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]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 865944451-Oleyl-3-palmitoylglycerolHCID 178443127HCID 178443127, compound

Product 1

HCID 865944461-Oleyl-3-palmitoyl-2-tetradecylthioacetylglycerolYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-oleyl-1-palmitoylglycerol (2 g, 0.003 mol) was dissolved in dichloromethane (150 ml) and dicyclohexylcarbodiimide (1.040 g, 0.005 mol), dimethylaminopyridine (0.616 g, 0.005 mol) and tetradecylthioacetic acid (1.455 g, 0.005 mol) were then added. The mixture was stirred at room temperature for 24 hours. The dicyclohexylurea precipitate was filtered, washed with dichloromethane and the filtrate was concentrated. The residue obtained was purified by silica gel chromatography (eluent:CH2Cl2-cyclohexane 4:6) to give the desired compound as an oil (yield: 49%).

Workup

  1. filtrationThe dicyclohexylurea precipitate was filtered
  2. washwashed with dichloromethane
  3. concentrationthe filtrate was concentrated
  4. customThe residue obtained
  5. customwas purified by silica gel chromatography (eluent:CH2Cl2-cyclohexane 4:6)

Sources & evidence

ORD record
ord-66d7bbffe532480ea9adacfd845ee7b3
Source dataset
uspto-grants-2008_05
Patent number
US07375135B2

Reaction notes

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