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 467947Notes

Reaction equation

HRID 467947 reaction equation
[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

Participants

7

Reactant 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

Product 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]-benzamideYield 24.6%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c51546f422944a78b0940089a05e3afa
Source dataset
uspto-grants-2014_01
Patent number
US08623896B2

Reaction notes

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