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Allyl bromide → 1-Allyl-3-benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid methyl ester

HRID 1622920
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1622920
Br[CH2:2][CH:3]=[CH2:4].[CH3:5][O:6][C:7]([C:9]1[C:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:13]([OH:23])[C:12]([C:24](=[O:34])[NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:11][N:10]=1)=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>CN(C)C=O>[CH3:5][O:6][C:7]([C:9]1[N:10]([CH2:4][CH:3]=[CH2:2])[CH:11]=[C:12]([C:24](=[O:34])[NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 178499094HCID 178499094, Verbindung

Produkt 1

HCID 596005921-Allyl-3-benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid methyl esterAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

After 3-bromopropene (2.15 ml, 24.8 mmol) was added to a solution of the compound 14 (6.79 g, 16.5 mmol), and cesium carbonate (8.09 g, 24.8 mmol) in dimethylformamide (54 ml), the mixture was stirred at room temperature for 4.5 hours. To the reaction solution was added an aqueous ammonium chloride solution, and this was extracted with ethyl acetate, washed with water and an aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was washed with diethyl ether to obtain 1-allyl-3-benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid methyl ester 15 (6.15 g, 83%) as a colorless crystal.

Aufarbeitung

  1. extractionthis was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialan aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. washthe residue was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-83d6754aaeb74ba2ac9f3217b7b8fd84
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08778943B2

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