Dicyclohexylcarbodiimide → Retinamide

HRID 429586

Reaktionsgleichung

Reaktionsgleichung von HRID 429586
C1([N:7]=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1[CH2:22][CH2:21][CH2:20][C:19]([CH3:24])([CH3:23])[C:18]=1/[CH:25]=[CH:26]/[C:27](/[CH3:37])=[CH:28]/[CH:29]=[CH:30]/[C:31](/[CH3:36])=[CH:32]/[C:33](O)=[O:34].ON1C2C=CC=CC=2N=N1>ClCCl>[CH3:16][C:17]1[CH2:22][CH2:21][CH2:20][C:19]([CH3:24])([CH3:23])[C:18]=1/[CH:25]=[CH:26]/[C:27](/[CH3:37])=[CH:28]/[CH:29]=[CH:30]/[C:31](/[CH3:36])=[CH:32]/[C:33]([NH2:7])=[O:34]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 444795Retinoic Acid

Produkt 1

HCID 5370221RetinamideAusbeute 208,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3.41 g (0.0165 mole) of dicyclohexylcarbodiimide (DCC) was added to 50 ml of dry dichloromethane solution of 6.98 g (0.0126 mole) of 1-amino-polyethyleneglycol-monomethyl ether (formula (IIIa), mean molecular weight 550), 4.54 g (0.0151 mole) of retinoic acid and 1.7 g (0.0126 mole) of 1-hydroxybenzotriazole and then stilled at room temperature for 8 hours in nitrogen atmosphere under shading and anhydrous condition. The reaction solution was filtered and then the solvent was removed by distillation under reduced pressure. The residue was separated by column chromatography (SiO2, mesh size 270-400, dichloromethane/methanol=15:1, v/v) to obtain 9.42 g (Yield 75%) of the title compound (pale yellow liquid in the form of wax, Tm=−15° C., Rf=0.22).

Aufarbeitung

  1. filtrationThe reaction solution was filtered
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residue was separated by column chromatography (SiO2, mesh size 270-400, dichloromethane/methanol=15:1

Quellen und Nachweise

ORD-Eintrag
ord-447fdee21405475a86ca6c4acf4dd660
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316644B1

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