Trifluoroacetamide → methyl 3-(furan-3-yl)-2-methoxy-6-{[S-phenyl-N-(trifluoroacetyl)sulphonimidoyl]methyl)benzoate

HRID 2177856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2177856
[C:1]1([S:7]([CH2:9][C:10]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([O:20][CH3:21])[C:13]([C:22]3[CH:26]=[CH:25][O:24][CH:23]=3)=[CH:12][CH:11]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:27][C:28]([F:33])([F:32])[C:29]([NH2:31])=[O:30].[O-2].[Mg+2].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[O:24]1[CH:25]=[CH:26][C:22]([C:13]2[C:14]([O:20][CH3:21])=[C:15]([C:10]([CH2:9][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[N:31][C:29](=[O:30])[C:28]([F:33])([F:32])[F:27])=[O:8])=[CH:11][CH:12]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:23]1

Komponenten

7

Edukt 4

HCID 67717TrifluoroacetamideHCID 6850729Magnesium monoxideHCID 12217721Iodo benzene diacetateHCID 67107600Methyl 6-(benzenesulphinylmethyl)-3-(furan-3-yl)-2-methoxybenzoate2×

Produkt 1

HCID 86677125methyl 3-(furan-3-yl)-2-methoxy-6-{[S-phenyl-N-(trifluoroacetyl)sulphonimidoyl]methyl)benzoateAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 423677Acetic acid, rhodium salt (4:2)KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of methyl 6-(benzenesulphinylmethyl)-3-(furan-3-yl)-2-methoxybenzoate (Intermediate 216, 0.920 g), trifluoroacetamide (0.56 g), magnesium oxide (0.40 g), iodobenzene diacetate (1.20 g) and rhodium (II) acetate dimer (0.030 g) in DCM (20 mL) was stirred at room temperature for 22 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica eluting with ethyl acetate and cyclohexane with a gradient of 10-40% to give methyl 3-(furan-3-yl)-2-methoxy-6-{[S-phenyl-N-(trifluoroacetyl)sulphonimidoyl]methyl}benzoate (0.46 g) as a colourless gum.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was purified by chromatography on silica eluting with ethyl acetate and cyclohexane with a gradient of 10-40%

Quellen und Nachweise

ORD-Eintrag
ord-5dd9645e16ca4e77b8d652443adddbb3
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067905B2

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