Ethanol → HCID 54037313, compound

HRID 486730Notes

Reaction equation

HRID 486730 reaction equation
[C:1]([C@@H:4]1[CH2:8][S:7][C@@H:6]([C:9]([SH:12])([CH3:11])[CH3:10])[CH2:5]1)([OH:3])=[O:2].C(=O)(O)[O-].[Na+].[CH2:18](O)[CH3:19]>S(=O)(=O)(O)O>[CH2:18]([O:2][C:1]([C@@H:4]1[CH2:8][S:7][C@@H:6]([C:9]([SH:12])([CH3:10])[CH3:11])[CH2:5]1)=[O:3])[CH3:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 54060056HCID 54060056, compound

Product 1

HCID 54037313HCID 54037313, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a stirred solution of trans-4-carboxy-2-(1-mercapto-1-methylethyl)tetrahydrothiophene (compound No. 8-1, 50 mg) in ethanol (3 ml), one drop of concentrated sulfuric acid was added under nitrogen atmosphere and the mixture was stirred for 1.5 hours. After cooling, the reaction mixture was week alkalized with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to give 53 mg of the titled compound (compound No. 12-1).

Workup

  1. temperatureAfter cooling
  2. waitthe reaction mixture was week
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-472db4b114cf41c8a6433cfdbe3c6531
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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