Methyl iodide → Methyl deoxycholate

HRID 1587020

Reaktionsgleichung

Reaktionsgleichung von HRID 1587020
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:28])[C@@H:13]([OH:27])[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][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[C:29](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:28])[C@@H:13]([OH:27])[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][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([O:7][CH3:29])=[O:6]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 222528Deoxycholic Acid

Produkt 1

HCID 229346Methyl deoxycholate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of deoxycholic acid (25.0 g) and anhydrous potassium carbonate (8.8 g) in anhydrous dimethylformamide (65 ml) is added methyl iodide (4.8 ml) and the mixture stirred at room temperature for about 4 hours. The mixture is diluted with ethyl acetate and washed four times with water and once with saturated sodium chloride solution. The organic solution is dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography in 80% ethyl acetate in hexane to give the desired product.

Aufarbeitung

  1. washwashed four times with water
  2. dry with materialThe organic solution is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash chromatography in 80% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-63bcb149b9b44fbcaceb542a47bf9caf
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05216015

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