[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide → methyl 4-((Z)-2-(2-(acetylamino)-5-[4-(methylthio)benzyl]-1,3-thiazol-4-yl)vinyl)benzoate

HRID 1246505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1246505
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1)=[O:5].CC(C)([O-])C.[K+].[CH:38]([C:40]1[N:41]=[C:42]([NH:54][C:55](=[O:57])[CH3:56])[S:43][C:44]=1[CH2:45][C:46]1[CH:51]=[CH:50][C:49]([S:52][CH3:53])=[CH:48][CH:47]=1)=O>CN(C=O)C>[C:55]([NH:54][C:42]1[S:43][C:44]([CH2:45][C:46]2[CH:47]=[CH:48][C:49]([S:52][CH3:53])=[CH:50][CH:51]=2)=[C:40](/[CH:38]=[CH:10]\[C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:31][CH:30]=2)[N:41]=1)(=[O:57])[CH3:56]

Komponenten

5

Edukt 3

HCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromideHCID 21914849N-{4-formyl-5-[4-(methylthio)benzyl]-1,3-thiazol-2-yl}acetamideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 86595605methyl 4-((Z)-2-(2-(acetylamino)-5-[4-(methylthio)benzyl]-1,3-thiazol-4-yl)vinyl)benzoateAusbeute 96,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide (4.81 g) and DMF (60 ml) were combined under N2 atmosphere. Then potassium tert-butoxide (1.32 g) and N-{4-formyl-5-[4-(methylthio)benzyl]-1,3-thiazol-2-yl}acetamide (3 g) were added to the suspension at 0° C. The reaction mixture was stirred at r.t. for 18 hours, poured into ice-water, and extracted with AcOEt. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with CHCl3/AcOEt (2:1) as an eluent. The solid was suspended in AcOEt, and the suspension was filtered. The filtrate was concentrated in vacuo to give methyl 4-((Z)-2-{2-(acetylamino)-5-[4-(methylthio)benzyl]-1,3-thiazol-4-yl}vinyl)benzoate (4.16 g) as a yellow amorphous substance.

Aufarbeitung

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography over silica gel with CHCl3/AcOEt (2:1) as an eluent
  6. filtrationthe suspension was filtered
  7. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c5d9a900d27946f6a43afbf0e48b094a
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07125901B2

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