Hydrochloric Acid → HCID 42622954, compound

HRID 1092447Notes

Reaction equation

HRID 1092447 reaction equation
C([O:4][C@H:5]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][CH:20]=3)[CH:12]=2)[C@@H:9]([O:27]C(=O)C)[C@H:8]([CH2:31][O:32]C(=O)C)[C@@H:7]([O:36]C(=O)C)[C@@H:6]1[O:40]C(=O)C)(=O)C.[OH-].[Na+].Cl>CO>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C@@H:10]2[C@@H:9]([OH:27])[C@H:8]([CH2:31][OH:32])[C@@H:7]([OH:36])[C@H:6]([OH:40])[C@H:5]2[OH:4])=[CH:12][C:13]=1[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH3:26])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57741109HCID 57741109, compound

Product 1

HCID 42622954HCID 42622954, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (1S,2R,3R,4S,5R,6R)-4-(acetoxymethyl)-6-(4-chloro-3-(4-ethylbenzyl)phenyl)cyclohexane-1,2,3,5-tetrayl tetraacetate (98 g, >99%, 0.158 mol, 1 eq) in methanol (1 L) was added sodium hydroxide (powder, 12.6 g, 0.315 mol, 2 eq) and the mixture was refluxed overnight. The mixture was acidified to pH 6 with 1 N hydrochloric acid and the volatiles were removed under reduced pressure. The residues were dissolved in ethyl acetate (3 L), washed with water (1 L), then with brine (1 L), dried over sodium sulfate, filtered and concentrated to give a white foam. The foam was recrystallized in refluxing ethanol/water (v/v=1:3, 20 mL/g (crude)) twice to give a white solid (58 g, purity of 99.3%, yield 90%).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customthe volatiles were removed under reduced pressure
  3. dissolutionThe residues were dissolved in ethyl acetate (3 L)
  4. washwashed with water (1 L)
  5. dry with materialwith brine (1 L), dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a white foam
  9. customThe foam was recrystallized
  10. temperaturein refluxing ethanol/water (v/v=1:3, 20 mL/g (crude)) twice
  11. customto give a white solid (58 g, purity of 99.3%, yield 90%)

Sources & evidence

ORD record
ord-4eb9a5d06fed43018fc5a07fd6c65644
Source dataset
uspto-grants-2012_03
Patent number
US08129434B2

Reaction notes

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