Hydrochloric Acid → HCID 178525783, compound

HRID 2370082Notes

Reaction equation

HRID 2370082 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]([O:19]C)=[O:18])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C@H:11]2[CH2:12][CH2:13][C@H:14]([C:17]([OH:19])=[O:18])[CH2:15][CH2:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178501294HCID 178501294, compound2×

Product 1

HCID 178525783HCID 178525783, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl trans-4-[(4-chlorophenyl) sulfonyl]cyclohexanecarboxylate (209 mg, 0.81 mol) synthesized in (10B) in methanol (10 ml), 2 N sodium hydroxide (0.5 ml, 1 mmol) was added at room temperature, and the resulting mixture was stirred at the same temperature for 1 hour. Then, to the reaction solution, 2 N hydrochloric acid (0.5 ml, 1 mmol) was added, and extraction was performed once with ethyl acetate. The obtained organic layer was washed with water and a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:90 to 0:100 (v/v)), whereby the title compound was obtained as an oil (180 mg, yield: 73%).

Workup

  1. additionwas added at room temperature
  2. extractionextraction
  3. washThe obtained organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:90 to 0:100 (v/v)), whereby the title compound

Sources & evidence

ORD record
ord-9c02b8c72633401ba84a56159bc8ecfc
Source dataset
uspto-grants-2014_04
Patent number
US08710060B2

Reaction notes

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