N-Hydroxysuccinimide → Oleic Acid
Reaction equation
[OH:1]N1C(=O)CCC1=O.CCN(C(C)C)C(C)C.[C:18](Cl)(=[O:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>C1COCC1>[C:18]([OH:36])(=[O:1])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
1.33 gr. of N-hydroxy succinimide (11.56 mmole, 1.5 eq.) and DIEA (1.35 ml), were dissolved in 50.0 ml of anhydrous THF and gently stirred at 0° C. under nitrogen atmosphere. Then, Oleoyl chloride (3.0 ml, 85% tech., 7.8 mmole, 1.0 eq.) dissolved in 50 ml of anhydrous THF was added dropwise during 1 h. The mixture was gently stirred for 2 h at 0° C. and over-night at room temperature. The resulting precipitate were discarded by filtration and the filtrate was evaporated under reduced pressure, redissolved in small amount of DCM and purified over silica-gel column using DCM as eluent. Fractions containing the product were combined and solvent was removed under reduced pressure. The resulting white solid was dried in vacuum over NaOH-pellets.
Workup
- additionwas added dropwise during 1 h
- stirringThe mixture was gently stirred for 2 h at 0° C. and over-night at room temperature
- filtrationThe resulting precipitate were discarded by filtration
- customthe filtrate was evaporated under reduced pressure
- dissolutionredissolved in small amount of DCM
- custompurified over silica-gel column
- additionFractions containing the product
- customsolvent was removed under reduced pressure
- dry with materialThe resulting white solid was dried in vacuum over NaOH-pellets
Sources & evidence
- ORD record
- ord-2c96b6da04b64e988f051a18427522d2
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06958325B2
Reaction notes
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