Hydrochloric Acid → HCID 57667874, compound

HRID 2191847Notes

Reaction equation

HRID 2191847 reaction equation
O1CCOCC1.[CH2:7]([C:15]1[CH:27]=[CH:26][C:18]([C:19]([O:21]C(C)(C)C)=[O:20])=[C:17]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N:35]3[CH:39]=[CH:38][CH:37]=[CH:36]3)[CH:30]=2)[CH:16]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+].Cl>C(OCC)(=O)C.CO>[CH2:7]([C:15]1[CH:27]=[CH:26][C:18]([C:19]([OH:21])=[O:20])=[C:17]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N:35]3[CH:39]=[CH:38][CH:37]=[CH:36]3)[CH:30]=2)[CH:16]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 68956473HCID 68956473, compound

Product 1

HCID 57667874HCID 57667874, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To dioxane 2.0 mL solution of tert-butyl 4-phenethyl-2-(3-(1H-pyrrol-1-yl)phenylamino)benzoate 83 mg were added methanol 2.0 mL and 2.0 mol/L sodium hydroxide aqueous solution 1.0 mL, and it was heated and refluxed for 3 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/L hydrochloric acid were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Diisopropyl ether was added to the obtained residue, and solid matter was filtrated to give 4-phenethyl-2-(3-(1H-pyrrol-1-yl)phenylamino)benzoic acid 36 mg of a white solid.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 3 hours
  3. customThe organic layer was separated
  4. washafter washing with saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure
  6. additionDiisopropyl ether was added to the obtained residue, and solid matter
  7. filtrationwas filtrated

Sources & evidence

ORD record
ord-00c3f18382294e4e816118e633cdce84
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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