Hydrochloric Acid → Methyl deoxycholate

HRID 586111

Reaction equation

HRID 586111 reaction equation
[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].Cl.[CH3:30]O>>[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][CH3:30])=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 222528Deoxycholic Acid

Product 1

HCID 229346Methyl deoxycholateYield 92%

Procedure

100 g of deoxycholic acid was dissolved in 300 ml of methanol, and then 2 ml of hydrochloric acid was added thereto. The resulting mixture was refluxed for 1 hour. The methanol was distilled off. After the resulting mixture was dissolved in 400 ml of ethylether, it was washed with distilled water, sodium bicarbonate and brine several times. The separated organic layer was dried over anhydrous magnesium sulfate, concentrated and dried in vacuo to prepare 95 g (yield: 92%) of methyl deoxycholate represented by the following formula:

Workup

  1. temperatureThe resulting mixture was refluxed for 1 hour
  2. distillationThe methanol was distilled off
  3. dissolutionAfter the resulting mixture was dissolved in 400 ml of ethylether
  4. washit was washed with distilled water, sodium bicarbonate and brine several times
  5. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1cca3e62b96c4d18a79d5b887c7271b8
Source dataset
uspto-grants-2005_08
Patent number
US06936402B2

Linked notes

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