Dimethylformamide → Arachidonyl-amine trifluoroacetate
Reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH2:19]([NH2:39])[CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>C(Cl)Cl>[CH2:19]([NH2:39])[CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a magnetically stirred solution of 69 mg (0.6 mmol) of trifluoroacetic acid, in 2 ml of dry methylene chloride, at 0° C., 0.046 ml (0.6 mmol) of dry DMF was added and then 0.3 ml (0.6 mmol) of 2.0 M solution of oxalyl chloride in methylene chloride, dropwise. The reaction mixture was stirred for 20 min and then a solution of 172 mg (0.6 mmol) of arachidonyl amine in 2 ml of methylene chloride was added and the reaction was stirred for 2 hrs at ambient temperature. The product was purified with silica gel column chromatography (eluents: petroleum ether/ethyl acetate, up to 50% ethyl acetate). Evaporation of the solvent, followed by Millipore filtration of a CH2Cl2 solution of the product gave 153 mg (0.4 mmol, 67% yield) of arachidonyl-amine-trifluoroacetate as a colorless oil.
Workup
- stirringthe reaction was stirred for 2 hrs at ambient temperature
- customThe product was purified with silica gel column chromatography (eluents
- customEvaporation of the solvent
- filtrationfollowed by Millipore filtration of a CH2Cl2 solution of the product
Sources & evidence
- ORD record
- ord-d289ba30bbed42288f2f70c75eaa0d07
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589220B2
Reaction notes
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