StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

2,2-Dimethyl-1,3-dioxane-4,6-dione → 2-chloro-4-[2-(4-fluorobenzyl)-3-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]benzonitrile

HRID 1173651
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1173651
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([C:20]([OH:22])=O)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH3:23][C:24]1(C)OC(=O)CC(=O)[O:25]1.S([O-])(O)(=O)=O.[K+]>CN(C1C=CN=CC=1)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C:24](=[O:25])[CH:23]=[C:20]([OH:22])[CH:11]2[CH2:12][C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 516920Potassium bisulfateHCID 67105225N-(3-chloro-4-cyanophenyl)-4-fluorophenylalanine

Produkt 1

HCID 595569272-chloro-4-[2-(4-fluorobenzyl)-3-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]benzonitrileAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N-(3-chloro-4-cyanophenyl)-4-fluorophenylalanine (3.67 g), Meldrum's acid (1.74 g) and 4-(N,N-dimethylamino)pyridine (2.11 g) in tetrahydrofuran (50 mL) was added N,N′-carbonyldiimidazole (2.24 g, 13.8 mmol) at 0° C., and the mixture was stirred at room temperature overnight. A 5% aqueous potassium hydrogen sulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with 5% aqueous potassium hydrogen sulfate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (50 mL), and the mixture was refluxed for 45 min. After allowing to room temperature, the organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was washed with ethyl acetate-isopropyl ether to give the title compound as colorless crystals (yield: 2.54 g, 64%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 5% aqueous potassium hydrogen sulfate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  6. temperaturethe mixture was refluxed for 45 min
  7. customAfter allowing to room temperature
  8. washthe organic layer was washed with water and saturated brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. washthe obtained residue was washed with ethyl acetate-isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-be38d993034241129575bde7ec10b6c4
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07834051B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion