Felbinac → N-methoxy-N-methyl-4-biphenylacetamide

HRID 449493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449493
Cl.[CH3:2][NH:3][O:4][CH3:5].[C:6]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:10][C:9]([CH2:12][C:13](O)=[O:14])=[CH:8][CH:7]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:6]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:10][C:9]([CH2:12][C:13]([N:3]([O:4][CH3:5])[CH3:2])=[O:14])=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 3332FelbinacHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Produkt 1

HCID 17815837N-methoxy-N-methyl-4-biphenylacetamideAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N,O-Dimethylhydroxylamine hydrochloride (550 mg, 5.6 mmol) was added to a mixture of biphenyl-4-ylacetic acid (Aldrich, Cat. #196487) (1 g, 5 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.5 g, 5.6 mmol), and N,N-diisopropylethylamine (1.6 mL, 9.4 mmol) in N,N-dimethylformamide (20 mL). The reaction was stirred for 3 h. at r.t., and was partitioned between water and ethyl acetate. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product, which was purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1) gave 2-biphenyl-4-yl-N-methoxy-N-methylacetamide (0.9 g, 70%) as a white solid. Analytical LCMS (M+H)+: m/z=255.9.

Aufarbeitung

  1. customwas partitioned between water and ethyl acetate
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product, which
  7. customwas purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c1ffd78b90804dddb0039c68c58076af
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481732B2

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