Acetamide → Benzyl-{2-[4-(2-methyl-oxazol-4-yl)-phenoxy]-ethyl]-carbamate

HRID 49392

Reaktionsgleichung

Reaktionsgleichung von HRID 49392
[C:1]([NH2:4])(=[O:3])[CH3:2].[CH2:5]([O:12][C:13](=[O:28])[NH:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=O)[CH2:25]Br)=[CH:20][CH:19]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[CH2:5]([O:12][C:13](=[O:28])[NH:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[N:4]=[C:1]([CH3:2])[O:3][CH:25]=2)=[CH:22][CH:23]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

3

Edukt 2

HCID 178AcetamideHCID 12986050Benzyl-[2-(4-bromoacetylphenoxy)-ethyl]-carbamate

Produkt 1

HCID 20587951Benzyl-{2-[4-(2-methyl-oxazol-4-yl)-phenoxy]-ethyl]-carbamateAusbeute 58 %

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Acetamide (2.95 g, 50.0 mmol) and benzyl-[2-(4-bromoacetylphenoxy)-ethyl]-carbamate (1.20 g, 3.06 mmol) were combined in a round-bottomed flask and heated to about 130° C. for about ninety minutes. The reaction mixture was then allowed to cool to room temperature, and the resulting orange solid was partitioned between ethyl acetate and water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude solid was purified by column chromatography (silica gel; methylene chloride to 10% ethyl acetate/methylene chloride) to afford 621 mg (58% yield) of the product as a white solid. LRMS ([M+H]+)=353.3.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customthe resulting orange solid was partitioned between ethyl acetate and water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude solid was purified by column chromatography (silica gel; methylene chloride to 10% ethyl acetate/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-8dfdc29225db4d1a972001c5c77782a5
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706743B2

Verknüpfte Notizen

Wird geladen…