Fenbufen → N-(4-azidobutyl)-4-(biphenyl-4-yl)-4-oxobutanamide

HRID 420410

Reaktionsgleichung

Reaktionsgleichung von HRID 420410
[CH:1]1[CH:2]=[CH:3][C:4]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([CH2:15][CH2:16][C:17]([OH:19])=O)=[O:14])=[CH:11][CH:12]=2)=[CH:5][CH:6]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[N:53]([CH2:56][CH2:57][CH2:58][CH2:59][NH2:60])=[N+:54]=[N-:55]>CC(C)=O.CCCCCC.CN(C=O)C>[N:53]([CH2:56][CH2:57][CH2:58][CH2:59][NH:60][C:17](=[O:19])[CH2:16][CH2:15][C:13]([C:10]1[CH:11]=[CH:12][C:7]([C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)=[CH:8][CH:9]=1)=[O:14])=[N+:54]=[N-:55]

Komponenten

7

Edukt 4

HCID 3335FenbufenHCID 81531DiisopropylethylamineHCID 1501111-Butanamine, 4-azido-HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 58554685N-(4-azidobutyl)-4-(biphenyl-4-yl)-4-oxobutanamideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21880519Acetone hexaneLösungsmittel

Versuchsvorschrift

A solution of fenbufen (214 mg, 0.8 mmol), HBTU (302 mg, 0.8 mmol), DIEA (1 mL, 0.8 mmol) and DMF (15 mL) was stirred. 4-azido-1-butanamine was added. TLC (acetone/n-hexane= 3/7) indicated the consumption of starting material (Rf=0.39) and the formation of the product (Rf=0.78). After stirring for 1 hr, the mixture was concentrated under high vacuum at 60° C. The residue was purified by flash chromatography using acetone: n-hexane=3:7 as eluents to provide a snow-white solid in 77% yield (269 mg).

Aufarbeitung

  1. customthe consumption of starting material (Rf=0.39)
  2. concentrationthe mixture was concentrated under high vacuum at 60° C
  3. customThe residue was purified by flash chromatography
  4. customn-hexane=3:7 as eluents to provide a snow-white solid in 77% yield (269 mg)

Quellen und Nachweise

ORD-Eintrag
ord-98b1634e93a64cb8be46531ac5ff23ad
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093427B2

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