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

HRID 2256235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2256235
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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 9821429[[3-(2-amino-1,2-dioxoethyl)-1-[(4-fluorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acidAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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 wtih 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.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 0.67 hours
  4. customthe aqueous layer separated
  5. extractionthe mixture extracted wtih 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

Quellen und Nachweise

ORD-Eintrag
ord-ea3710535afb487f847d3d8b1113fdc5
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05654326

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