Methanol → [[3-(2-amino-1,2-dioxoethyl)1-[(2,6-dichlorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid

HRID 3353Notes

Reaction equation

HRID 3353 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([C:25](=[O:29])[C:26]([NH2:28])=[O:27])=[C:9]([CH3:24])[N:10]2[CH2:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:23].[OH-].[Na+].CO.C(OCC)(=O)C>O>[NH2:28][C:26](=[O:27])[C:25]([C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH2:4][C:3]([OH:30])=[O:2])[N:10]([CH2:15][C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])[C:9]=1[CH3:24])=[O:29]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 11797741HCID 11797741, compound

Product 1

HCID 9889171[[3-(2-amino-1,2-dioxoethyl)1-[(2,6-dichlorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acidYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 420 mg (0.94 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-[(2,6-dichlorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl ester, 5 mL of 1N NaOH and 15 mL of MeOH was heated to maintain reflux for 0.17 hours, cooled to room temperature and stirred 0.5 hours. Ethyl acetate and water was added, the aqueous layer separated, made acidic to pH 2-3 with 1N HCl, and the mixture extracted with ethyl acetate two times. The part that was not soluble was filtered. The filtrate was dried (MgSO4) and concentrated. The remaining solid was washed with a small volume of ether/methylene chloride and the insoluble material filtered and combined with the filtered material above to give 351 mg (86% yield) of [[3-(2-amino-1,2-dioxoethyl)-1-[(2,6-dichlorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid, mp, 236°-239° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 0.17 hours
  4. customthe aqueous layer separated
  5. extractionthe mixture extracted with ethyl acetate two times
  6. filtrationThe part that was not soluble was filtered
  7. dry with materialThe filtrate was dried (MgSO4)
  8. concentrationconcentrated
  9. washThe remaining solid was washed with a small volume of ether/methylene chloride
  10. filtrationthe insoluble material filtered

Sources & evidence

ORD record
ord-06734e09bf9f433d9b3795926278123c
Source dataset
uspto-grants-1998_03
Patent number
US05733923

Reaction notes

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