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

HRID 3357Notes

Reaction equation

HRID 3357 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([C:24](=[O:28])[C:25]([NH2:27])=[O:26])=[C:9]([CH3:23])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1.[OH-].[Na+].CO.C(OCC)(=O)C>O>[NH2:27][C:25](=[O:26])[C:24]([C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH2:4][C:3]([OH:29])=[O:2])[N:10]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[C:9]=1[CH3:23])=[O:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 10524900HCID 10524900, compound

Product 1

HCID 9821429[[3-(2-amino-1,2-dioxoethyl)-1-[(4-fluorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acidYield 81.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 767 mg (1.9 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-[(4-fluorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl ester, 10 mL of 1N NaOH and 30 mL of MeOH was heated to maintain reflux for 0.67 hours, cooled to room temperature and stirred 1 hour. Ethyl acetate and water were added and the aqueous layer separated, made acidic to pH 2-3 with 1N HCl and the mixture extracted with ethyl acetate two times. The combined ethyl acetate extracts were dried (MgSO4) and concentrated. The remaining solid was washed with a small volume of ethyl acetate to give 593 mg (81% yield) of [[3-(2-amino-1,2-dioxoethyl)-1-[(4-fluorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid, mp, 244°-247° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 0.67 hours
  4. customthe aqueous layer separated
  5. extractionthe mixture extracted with ethyl acetate two times
  6. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  7. concentrationconcentrated
  8. washThe remaining solid was washed with a small volume of ethyl acetate

Sources & evidence

ORD record
ord-1f91a3ebc06246c6a616154657ef7250
Source dataset
uspto-grants-1998_03
Patent number
US05733923

Reaction notes

Loading…