Hydrochloric Acid → 2-(9-Benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl) acetic acid

HRID 1417484Notes

Reaction equation

HRID 1417484 reaction equation
[OH-].[K+].[CH2:3]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]2[CH2:19][CH2:20][CH:21]([CH2:23][C:24]([O:26]CC)=[O:25])[S:22][C:11]1=2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>C(O)C>[CH2:3]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]2[CH2:19][CH2:20][CH:21]([CH2:23][C:24]([OH:26])=[O:25])[S:22][C:11]1=2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 53821095HCID 53821095, compound

Product 1

HCID 545749702-(9-Benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl) acetic acidYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.5 ml of a 3% w/v aqueous solution of potassium hydroxide was added to a mixture of 44 mg of ethyl 2-(9-benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl)acetate (prepared as described in Example 82) in 2 ml of ethanol. The reaction mixture was then stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was made acidic by the addition of a 3% w/v aqueous solution of hydrochloric acid and extracted with ethyl acetate. The ethyl acetate fraction was then washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was recrystallized from hexane and ethyl acetate to afford 37 mg of the title compound as a solid which melted at 164°-167° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate fraction was then washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was then removed by evaporation under reduced pressure
  5. customthe resulting residue was recrystallized from hexane and ethyl acetate

Sources & evidence

ORD record
ord-0c7239ca1e4247229d8493b3d1851401
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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