Cholic Acid → Apocholic acid

HRID 1587032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587032
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:29])[C@@H:13]([OH:28])[CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23]([OH:25])[CH2:24][C@H:19]4[CH2:18][C@@H:17](O)[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6]>CC(C)=O.[Cl-].[Zn+2].[Cl-]>[OH:25][C@@H:23]1[CH2:22][CH2:21][C@@:20]2([CH3:26])[C@H:19]([CH2:18][CH2:17][C:16]3[C@@H:15]2[CH2:14][C@H:13]([OH:28])[C@@:12]2([CH3:29])[C:11]=3[CH2:10][CH2:9][C@@H:8]2[C@H:2]([CH3:1])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])[CH2:24]1

Komponenten

4

Edukt 1

HCID 221493Cholic Acid

Produkt 1

HCID 101818Apocholic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of cholic acid (11.4 g) and zinc chloride (13 g) in acetone (50 ml) is heated so as to distil off solvent, then heated at an external temperature of 110° C. for about 1.5 hours. The mixture is poured into water, extracted with ether and the organic solution dried over magnesium sulfate, dried, filtered, and concentrated in vacuo. The crude is purified by flash chromatography to give the desired product.

Aufarbeitung

  1. temperatureis heated so as
  2. customto distil off solvent
  3. additionThe mixture is poured into water
  4. extractionextracted with ether
  5. dry with materialthe organic solution dried over magnesium sulfate
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ece4ca440c0644d1b45c6272a01696a0
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05216015

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