Hydrochloric Acid → HCID 66738112, compound

HRID 722005Notes

Reaction equation

HRID 722005 reaction equation
[OH:1][C@@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@H:4]([C@@H:5]([CH2:31]C)[C@@H:6]([OH:30])[C@@H:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH2:3]1.[OH-].[Na+].Cl>CCO>[OH:1][C@@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@H:4]([C@@H:5]([CH3:31])[C@@H:6]([OH:30])[C@@H:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11396723HCID 11396723, compound

Product 1

HCID 66738112HCID 66738112, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ethyl 3α,7α-dihydroxy-6α-ethyl-5β-cholan-24-oate (4) (0.10 g, 0.22 mmol) was dissolved in 15 ml of 96% EtOH and added to 10% NaOH in 96% EtOH (2 ml, 5 mmol). The mixture was refluxed for 4 hours. The mixture was acidified with 3N HCl and extracted with ethyl acetate (3×20 ml). The combined organic fractions were washed with a saturated NaCl solution (1×50 ml), dried with Na2SO4 and evaporated under vacuum. The residue was chromatographed on silica gel column; elution by CHCl3:MeOH (95:5) yielded 3α,7α-dihydroxy-6α-methyl-5β-cholan-24-oic acid (6) (0.04 g, 0.095 mmol, 43% yield).

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. washThe combined organic fractions were washed with a saturated NaCl solution (1×50 ml)
  4. dry with materialdried with Na2SO4
  5. customevaporated under vacuum
  6. customThe residue was chromatographed on silica gel column
  7. washelution by CHCl3:MeOH (95:5)

Sources & evidence

ORD record
ord-87318d357c5e460ca81f2a4397ad597e
Source dataset
uspto-grants-2006_11
Patent number
US07138390B2

Reaction notes

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