Hydrochloric Acid → HCID 57879318, compound

HRID 1673547Notes

Reaction equation

HRID 1673547 reaction equation
CO.[OH-].[Na+].[O:5]([C:12]1[CH:24]=[CH:23][C:15]([C:16]([O:18]C(C)(C)C)=[O:17])=[C:14]([NH:25][C:26](=[O:38])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([N:33]3[CH:37]=[CH:36][CH:35]=[CH:34]3)[CH:28]=2)[CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>C(OCC)(=O)C.O1CCOCC1>[O:5]([C:12]1[CH:24]=[CH:23][C:15]([C:16]([OH:18])=[O:17])=[C:14]([NH:25][C:26](=[O:38])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([N:33]3[CH:37]=[CH:36][CH:35]=[CH:34]3)[CH:28]=2)[CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67344182tert-butyl 4-phenoxy-2-(3-(1H-pyrrol-1-yl)benzamido)benzoate

Product 1

HCID 57879318HCID 57879318, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

1.0 mL of methanol and 0.5 mL of 2.0 mol/L aqueous sodium hydroxide were added to 1.0 mL of dioxane solution containing 20 mg of tert-butyl 4-phenoxy-2-(3-(1H-pyrrol-1-yl)benzamido)benzoate at room temperature and stirred at 50° C. for 30 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/L hydrochloric acid were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. Diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 7.6 mg of 4-phenoxy-2-(3-(1H-pyrrol-1-yl)benzamido)benzoic acid as white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washafter washed with a saturated sodium chloride aqueous solution
  5. customthe solvent was evaporated under reduced pressure
  6. additionDiisopropyl ether were added to the obtained residue
  7. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-6bd5204c3aa1498a90237654e9387b80
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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