Hydrochloric Acid → HCID 17755103, compound

HRID 1957935Notes

Reaction equation

HRID 1957935 reaction equation
[CH3:1][CH:2]([CH2:7][C@H:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C@@H:17]([CH2:18][C@H:19]([OH:29])[CH2:20][CH2:21]2)[CH2:16][C@H:15]3[OH:30])[CH2:12][CH2:11]1)[CH3:9])[C:3]([O:5]C)=[O:4].[OH-].[Na+].Cl>CO>[CH3:1][C@@H:2]([CH2:7][C@H:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C@@H:17]([CH2:18][C@H:19]([OH:29])[CH2:20][CH2:21]2)[CH2:16][C@H:15]3[OH:30])[CH2:12][CH2:11]1)[CH3:9])[C:3]([OH:5])=[O:4].[CH3:1][C@H:2]([CH2:7][C@H:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C@@H:17]([CH2:18][C@H:19]([OH:29])[CH2:20][CH2:21]2)[CH2:16][C@H:15]3[OH:30])[CH2:12][CH2:11]1)[CH3:9])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 17755006HCID 17755006, compound

Product 2

HCID 17755103HCID 17755103, compoundYield 65%HCID 17755105HCID 17755105, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 23-methyl-3α,7α-dihydroxy-5β-cholan-24-oate 0.97 g (2.3 mmol) was dissolved in MeOH (25 mL) and added with 10% NaOH in MeOH (5.7 mL, 14.2.mmol). The mixture was refluxed for 16 h. The mixture was acidified with 3N HCl and extracted with EtOAc (3×20 mL). The combined organic fractions were washed with brine (1×50 mL), dried (Na2SO4) and evaporated under vacuum. The residue was purified by silica gel flash chromatography. Elution with CHCl3:MeOH (95/5) afforded 1.5 g (65%) of 23(S)-Methyl-3α,7α-dihydroxy-5β-cholan-24-oic acid and 330 mg of 23(R)-Methyl-3α,7α-dihydroxy-5β-cholan-24-oic acid.

Workup

  1. temperatureThe mixture was refluxed for 16 h
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined organic fractions were washed with brine (1×50 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated under vacuum
  6. customThe residue was purified by silica gel flash chromatography
  7. washElution with CHCl3

Sources & evidence

ORD record
ord-5713ec8692ef47d097eebbfd1e544e5e
Source dataset
uspto-grants-2013_04
Patent number
US08410083B2

Reaction notes

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