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

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.

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

ORD record

ord-0c7239ca1e4247229d8493b3d1851401

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05877199