Methanol → Chenodeoxycholic Acid

HRID 2199017Notes

Reaction equation

HRID 2199017 reaction equation
CO.[OH-].[K+].C([O:8][C@@H:9]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C@H:11]([CH2:12][C@@H:13]([O:36]C(=O)C)[C@@H:14]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:35])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:26])[CH2:20][CH2:21][C:22]([O:24]C)=[O:23])[CH2:10]1)(=O)C>C(O)(C)C>[CH3:26][C@@H:19]([C@@H:18]1[C@@:27]2([CH3:35])[CH2:28][CH2:29][C@@H:30]3[C@@:31]4([CH3:34])[CH2:32][CH2:33][C@@H:9]([OH:8])[CH2:10][C@H:11]4[CH2:12][C@@H:13]([OH:36])[C@H:14]3[C@@H:15]2[CH2:16][CH2:17]1)[CH2:20][CH2:21][C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 11466003Chenodeoxycholic acid diacetate methyl ester

Product 1

HCID 10133Chenodeoxycholic AcidYield 69.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 3 ml of methanol, 5 ml of isopropanol and 0.8 g of potassium hydroxide was added 0.294 g (0.000599 mol) of methyl 3α,7α-diacetyloxy-5β-cholan-24-oate. The mixture was heated to reflux under an argon atmosphere for 4 hr. then stirred overnight at room temperature. The solvents were removed in vacuo. The mixture was acidified with 1 N HCl and extracted with 3×25 ml of ethyl acetate. The combined ethyl acetate extracts were washed with water then dried over anhydrous sodium sulfate. The mixture was filtered and solvents removed in vacuo. The residue were recrystallized from ethyl acetate to give 0.163 g (69.3%) of chenodeoxycholic acid, mp 117°-118° C., which did not depress when mixed with authentic material (mp 117°-118° C. from ethyl acetate).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under an argon atmosphere for 4 hr
  3. customThe solvents were removed in vacuo
  4. extractionextracted with 3×25 ml of ethyl acetate
  5. washThe combined ethyl acetate extracts were washed with water
  6. dry with materialthen dried over anhydrous sodium sulfate
  7. filtrationThe mixture was filtered
  8. customsolvents removed in vacuo
  9. customThe residue were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0d6f9aefa3fb4505af7c0c11c2748644
Source dataset
uspto-grants-1982_11
Patent number
US04360470

Reaction notes

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