Trifluoroacetamide → 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[1-oxo-1-(2,2,2-trifluoro-acetylimino)-thietan-3-yl]-benzamide

HRID 467947

反応式

HRID 467947 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:29]([F:32])([F:31])[F:30])[O:13][N:12]=[C:11]([C:14]3[CH:27]=[CH:26][C:17]([C:18]([NH:20][CH:21]4[CH2:24][S:23](=[O:25])[CH2:22]4)=[O:19])=[C:16]([CH3:28])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[F:33][C:34]([F:39])([F:38])[C:35]([NH2:37])=[O:36].[O-2].[Mg+2].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>ClCCl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:29]([F:31])([F:30])[F:32])[O:13][N:12]=[C:11]([C:14]3[CH:27]=[CH:26][C:17]([C:18]([NH:20][CH:21]4[CH2:22][S:23](=[O:25])(=[N:37][C:35](=[O:36])[C:34]([F:39])([F:38])[F:33])[CH2:24]4)=[O:19])=[C:16]([CH3:28])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

参加物

7

反応物 4

HCID 67717TrifluoroacetamideHCID 6850729Magnesium monoxideHCID 12217721Iodo benzene diacetateHCID 595634974-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-(1-oxo-thietan-3-yl)-benzamide

生成物 1

HCID 595634894-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[1-oxo-1-(2,2,2-trifluoro-acetylimino)-thietan-3-yl]-benzamide収率 24.6%

試薬・触媒・溶媒 2

HCID 152122Dirhodium tetraacetate触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-(1-oxo-thietan-3-yl)-benzamide (Example P2) (0.2 g) in dichloromethane (20 ml) was added trifluoroacetamide (0.09 g), rhodium(II) acetate dimer (0.02 g), magnesium oxide (0.07 g) and iodobenzene diacetate (0.19 g). The reaction mixture was stirred at ambient temperature for 42 hours. The reaction mixture was concentrated and the residue purified by chromatography on silica gel (eluent: ethyl acetate/heptane 1:1) to give 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[1-oxo-1-(2,2,2-trifluoro-acetylimino)-thietan-3-yl]-benzamide (0.06 g) as an off-white powder. HPLC-MS: RT 2.14 min and 2.18 min (two isomers) MH+ 616.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by chromatography on silica gel (eluent: ethyl acetate/heptane 1:1)

出典と根拠

ORDレコード
ord-c51546f422944a78b0940089a05e3afa
出典データセット
uspto-grants-2014_01
特許番号
US08623896B2

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