Dicyclohexylcarbodiimide → (5Z,8Z,11Z,14Z)-16-Hydroxy-5,8,11,14-eicosatetraenoic acid

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Reaktionsgleichung

[OH:1][CH:2]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=[CH:16][C:17]([OH:19])=[O:18].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:23][CH2:22][CH2:21][CH2:20][CH:2]([OH:1])/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

An equimolar mixture of 16-hydroxyeicosatetraenoic acid (16 HETE) and N-hydroxysuccinimide in anhydrous tetrahydrofuran (THF) was cooled to 0° C. To this was added 1 equivalent of dicyclohexylcarbodiimide (DCC) with stirring. After 12h at room temperature, the solvent was removed in vacuo and the residue was purified by SiO2 chromatography to afford the corresponding 16-HETE N-hydroxysuccimide ester in 75% yield as a colorless oil.

Aufarbeitung

customAfter 12h at room temperature, the solvent was removed in vacuo
customthe residue was purified by SiO2 chromatography

Quellen und Nachweise

ORD-Eintrag: ord-ea8cd371ee024e73adc800ddbeed98ea
Quelldatensatz: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06562988B2

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