Hydrochloric Acid → HCID 19603672, compound

HRID 1604686Notes

Reaction equation

HRID 1604686 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([CH2:29][CH:30](C(OCC)=O)[C:31]([O:33]CC)=[O:32])=[CH:26][CH:27]=5)[C:22]([C:41]#[N:42])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:26][CH:27]=5)[C:22]([C:41]#[N:42])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19603745HCID 19603745, compound

Product 1

HCID 19603672HCID 19603672, compoundYield 130.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 3-{1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-3-cyanoindol-5-yl}-2-ethoxycarbonylpropionate (0.72 g) and 1N sodium hydroxide solution (5 ml) in methanol (10 ml) was stirred under reflux for 3 hours. After cooling, the mixture was made acidic with diluted hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was dissolved in xylene (10 ml) containing acetic acid (7.5 ml) and the mixture was stirred under reflux for 7 hours. After removal of solvent by evaporation, the residue was partitioned between diluted hydrochloric acid and ethyl acetate. The ethyl acetate layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatogaphy on silica gel and eluted with a mixture of chloroform and methanol. The fractions containing the objective compounds were combined and concentrated under reduced pressure to give 3-{1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-3-cyanoindol-5-yl}propionic acid (0.78 g).

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. dissolutionThe residue was dissolved in xylene (10 ml)
  8. additioncontaining acetic acid (7.5 ml)
  9. stirringthe mixture was stirred
  10. temperatureunder reflux for 7 hours
  11. customAfter removal of solvent
  12. customby evaporation
  13. customthe residue was partitioned between diluted hydrochloric acid and ethyl acetate
  14. washThe ethyl acetate layer was washed with water and brine
  15. dry with materialdried over magnesium sulfate
  16. customevaporated under reduced pressure
  17. washeluted with a mixture of chloroform and methanol
  18. additionThe fractions containing the objective compounds
  19. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3dc29edf55c34316ad668207b288f57c
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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