Ammonium trifluoroacetate → HCID 178468520, Verbindung

HRID 545344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 545344
[CH2:1]([O:3][C:4](=[O:39])[CH:5]([N:22]([CH:36]1[CH2:38][CH2:37]1)[C:23](=O)[C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1)[C:6]([C:8]1[CH:9]=[N:10][C:11]([O:14]CC2C=CC=CC=2)=[CH:12][CH:13]=1)=O)[CH3:2].FC(F)(F)C([O-])=O.[NH4+:47]>CCO>[CH2:1]([O:3][C:4]([C:5]1[N:22]([CH:36]2[CH2:38][CH2:37]2)[C:23]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=2)=[N:47][C:6]=1[C:8]1[CH:9]=[N:10][C:11]([OH:14])=[CH:12][CH:13]=1)=[O:39])[CH3:2]

Komponenten

4

Edukt 2

HCID 2724268Ammonium trifluoroacetateHCID 671330303-(6-Benzyloxy-pyridin-3-yl)-2-[cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-propionic acid ethyl ester

Produkt 1

HCID 178468520HCID 178468520, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To 1.4 g (3 mmol) of 3-(6-benzyloxy-pyridin-3-yl)-2-[cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-propionic acid ethyl ester in 5 ml of EtOH was added 1.4 g (10 mmol) of ammonium trifluoroacetate. The EtOH was evaporated and the residue heated to 110° C. for 16 h. The cooled residue was partitioned between saturated sodium hydrogen carbonate solution and CH2Cl2. The organic phase was dried with sodium sulfate and concentrated. The crude reside was re-dissolved in 10 ml of EtOH, a generous spatula of 10% palladium on activated charcoal was added, and the mixture stirred under an atmosphere of hydrogen for 1 h. The mixture was then filtered over Hyflo and concentrated. Purification by flash column chromatography [MeOH/EtOAc 4:96 to 1:9] afforded 0.8 g (70%) of the title compound as a colorless solid. MS: 434.2 (MH+).

Aufarbeitung

  1. customThe EtOH was evaporated
  2. customThe cooled residue was partitioned between saturated sodium hydrogen carbonate solution and CH2Cl2
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated
  5. dissolutionThe crude reside was re-dissolved in 10 ml of EtOH
  6. additiona generous spatula of 10% palladium on activated charcoal was added
  7. filtrationThe mixture was then filtered over Hyflo
  8. concentrationconcentrated
  9. customPurification by flash column chromatography [MeOH/EtOAc 4:96 to 1:9]

Quellen und Nachweise

ORD-Eintrag
ord-cdccb0f9c152460cbf2ef451354e1a15
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935707B2

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