Dimethylformamide → HCID 70467670, Verbindung

HRID 64736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64736
[C:1]([OH:9])(=[O:8])[CH:2]([CH2:4][CH:5]([CH3:7])[CH3:6])[OH:3].[OH-].[Na+].[CH2:12]([C@H:14]1[CH2:19][C@H:18]2[C@H:20]3[C@H:29]([CH2:30][CH2:31][C@:16]2([CH3:17])[C@H:15]1[O:33][C:34](=[O:37])[CH2:35]Br)[C@@H:28]1[C:23](=[CH:24][C:25](=[O:32])[CH2:26][CH2:27]1)[CH2:22][CH2:21]3)[CH3:13].CN(C=O)C>CC(C)=O>[CH2:12]([C@H:14]1[CH2:19][C@H:18]2[C@H:20]3[C@H:29]([CH2:30][CH2:31][C@:16]2([CH3:17])[C@H:15]1[O:33][C:34](=[O:37])[CH2:35][O:8][C:1](=[O:9])[CH:2]([OH:3])[CH2:4][CH:5]([CH3:7])[CH3:6])[C@@H:28]1[C:23](=[CH:24][C:25](=[O:32])[CH2:26][CH2:27]1)[CH2:22][CH2:21]3)[CH3:13]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 92779(+-)-2-Hydroxyisocaproic acidHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Produkt 1

HCID 70467670HCID 70467670, VerbindungAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

In 2.0 ml of acetone is dissolved 0.26 g of leucic acid, and 1.0 ml of 2N-NaOH is added, followed by addition of 0.44 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 15 ml of DMF. The mixture is refluxed for 3 hours, and thereafter treated in the same manner as Example 26. The reaction mixture is then subjected to column chromatography. Following passage of 50 ml of diisopropyl ether-n-hexane (1:1), elution is carried out with 200 ml of diisopropyl ether. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.475 g of the above-identified compound as a viscous oil.

Aufarbeitung

  1. additionis added
  2. temperatureThe mixture is refluxed for 3 hours
  3. additiontreated in the same manner as Example 26
  4. washpassage of 50 ml of diisopropyl ether-n-hexane (1:1), elution
  5. customThe eluate is evaporated under reduced pressure
  6. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-8d75143b7589477eb7b0b8c2e8274815
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04609650

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