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

HRID 2177856Notes

Reaction equation

HRID 2177856 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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%

Sources & evidence

ORD record
ord-5dd9645e16ca4e77b8d652443adddbb3
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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