Cholic Acid → Apocholic acid

HRID 1587032Notes

Reaction equation

HRID 1587032 reaction equation
[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

Participants

4

Reactant 1

HCID 221493Cholic Acid

Product 1

HCID 101818Apocholic acid

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
110 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ece4ca440c0644d1b45c6272a01696a0
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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