Water → (R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid amide

HRID 273177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 273177
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[CH2:16][C@@H:15]([C:19](O)=[O:20])[CH2:14]2)=[CH:9][CH:8]=1.C(N1C=CN=C1)([N:27]1C=CN=C1)=O.C([O-])(=O)C.[NH4+].O>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[CH2:16][C@@H:15]([C:19]([NH2:27])=[O:20])[CH2:14]2)=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 517165Ammonium AcetateHCID 67411567(R)-1-(4-((3-Fluorobenzyl)oxy)phenyl)-5-oxopyrrolidine-3-carboxylic acid

Produkt 1

HCID 11529971(R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid (1.5 g, 0.005 mol) was dissolved in dry N,N-dimethylformamide under argon and cooled to 0° C. 1,1′-Carbonyl-diimidazole (1.4 g, 0.009 mol) was added to the mixture and the reaction stirred for one hour while the temperature rose from 0° C. to room temperature. Ammonium acetate (5.6 g, 0.073 mol) was added and the reaction was stirred for one hour at room temperature. Water was added dropwise to the mixture and a precipitate appeared. The solid was filtrated, washed with water and dried under vacuum to yield 1.36 g (0.0041 mol, 91% of theory) of the title compound as a white solid. MS (m/e)=329.3(M+H)+.

Aufarbeitung

  1. customrose from 0° C. to room temperature
  2. stirringthe reaction was stirred for one hour at room temperature
  3. filtrationThe solid was filtrated
  4. washwashed with water
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a391ba6512034064a12f9a5416bcd101
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456210B2

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