Hydrochloric Acid → HCID 54522329, compound

HRID 2292762Notes

Reaction equation

HRID 2292762 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17]CC)=[O:16])[CH:13]=2)[N:8]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:7]=1[CH3:27])[CH3:2].[OH-].[Na+].Cl>CCO>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([OH:17])=[O:16])[CH:13]=2)[N:8]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:7]=1[CH3:27])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 54201863HCID 54201863, compound

Product 1

HCID 54522329HCID 54522329, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.6 g (4.2 mmol) of 5-ethoxycarbonyl-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid ethyl ester and 4.2 mL of 1N NaOH in 75 mL of EtOH was stirred 2.25 hours, 10 mL of 1N NaOH added, and stirred an additional 18.5 hours. The reaction mixture was acidified with 1N HCl, extracted with EtOAc, the EtOAc solution washed with saturated NaCl solution, dried (Na2SO4), and concentrated at reduced pressure. The residue was heated in 150 mL of EtOH for 4.5 hours, and left at room temperature for 96 hours. After concentrating at reduced pressure, the residue was chromatographed on silica (25% ether/hexane→50% ether/hexane) to give 110 mg (7.5% yield) of 5-carboxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid ethyl ester.

Workup

  1. extractionextracted with EtOAc
  2. washthe EtOAc solution washed with saturated NaCl solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated at reduced pressure
  5. temperatureThe residue was heated in 150 mL of EtOH for 4.5 hours
  6. waitleft at room temperature for 96 hours
  7. concentrationAfter concentrating at reduced pressure
  8. customthe residue was chromatographed on silica (25% ether/hexane→50% ether/hexane)

Sources & evidence

ORD record
ord-330c56423011406cb57f395cb7a8dc3b
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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