HCID 10763855, Verbindung → [[3-(2-amino-1,2-dioxoethyl)-2-cyclopropyl-1-(phenylmethyl)-1H-indol-4-yl]oxy)acetic acid

HRID 2256255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2256255
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]([CH:22]1[CH2:24][CH2:23]1)[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[OH-].[Na+].CO>[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[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]=1[CH:22]1[CH2:24][CH2:23]1)=[O:29]

Komponenten

4

Edukt 1

HCID 10763855HCID 10763855, Verbindung

Produkt 1

HCID 9908515[[3-(2-amino-1,2-dioxoethyl)-2-cyclopropyl-1-(phenylmethyl)-1H-indol-4-yl]oxy)acetic acidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A mixture of 220 mg (0.54 mmol) of [[3-(2-amino-1,2-dioxoethyl)-2-cyclopropyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester in 5 mL of 1N NaOH and 15 mL of MeOH was heated to maintain reflux for 0.67 hours, concentrated at reduced pressure and the residue taken up in EtOAc/water. The aqueous layer was separated, made acidic with 1N HCl to pH 2-3 and EtOAc added. A precipitate formed and was separated to give 169 mg (80% yield) of [[3-(2-amino-1,2-dioxoethyl)-2-cyclopropyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid, mp, 246°-249° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 0.67 hours
  4. concentrationconcentrated at reduced pressure
  5. customThe aqueous layer was separated
  6. additionadded
  7. customA precipitate formed
  8. customwas separated

Quellen und Nachweise

ORD-Eintrag
ord-7d3be30f1bea44b29468a28b2d58416b
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05654326

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