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

HRID 2177856ノート

反応式

HRID 2177856 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 86677125methyl 3-(furan-3-yl)-2-methoxy-6-{[S-phenyl-N-(trifluoroacetyl)sulphonimidoyl]methyl)benzoate収率 38.5%

試薬・触媒・溶媒 2

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-5dd9645e16ca4e77b8d652443adddbb3
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

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