4-Nitrophenol → 10-Methylundecanoic acid

HRID 1780704

Reaktionsgleichung

Reaktionsgleichung von HRID 1780704
C[CH:2](C)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[N+]([C:19]1C=CC(O)=CC=1)([O-])=O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH3:19][CH:3]([CH3:2])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Komponenten

5

Edukt 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 33002Isotridecanoic acid

Produkt 1

HCID 7594210-Methylundecanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 11-methyldodecanoic acid (400 mg) and para-nitrophenol (260 mg) dissolved in N,N-dimethylformamide (DMF, 30 ml) was added N,N'-dicyclohexylcarbodiimide (385 mg), and the mixture was stirred for 12 hours. The reaction mixture was filtered and concentrated to give the active ester of 10-methylundecanoic acid. To the active ester (620 mg), after having been dissolved in DMF, were added 6-(4'-N-glycyl-spicaminyl-amino)purine hydrochloride (710 mg) and triethylamine (2.0 ml), and the mixture was stirred for 12 hours. The solvent was removed by distillation, and the residue was subjected to chromatography on a silica gel column with eluent systems of chloroform-methanol (from 7:1 to 5:1) to give SPK251 in the yield of 236 mg.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-348485e64166449e857ebc7ebe4eeff6
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05631238

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