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

반응식

HRID 467947 반응식
[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

참가 물질

7

반응물 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

생성물 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]-benzamide수율 24.6%

시약·촉매·용매 2

HCID 152122Dirhodium tetraacetate촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-c51546f422944a78b0940089a05e3afa
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623896B2

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