Trifluoroacetamide → HCID 86707844, compound

HRID 1844669Notes

Reaction equation

HRID 1844669 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[O:5][C:6]1[CH:7]([CH2:20][CH:21]2[CH2:26][CH2:25][S:24](=[O:27])[CH2:23][CH2:22]2)[NH:8][C:9](=[O:19])[C:10]=1[C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[CH3:18])[CH3:2].[F:29][C:30]([F:35])([F:34])[C:31]([NH2:33])=[O:32].C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C>C(Cl)Cl.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH2:1]([O:3][C:4](=[O:28])[O:5][C:6]1[CH:7]([CH2:20][CH:21]2[CH2:26][CH2:25][S:24](=[O:27])(=[N:33][C:31](=[O:32])[C:30]([F:35])([F:34])[F:29])[CH2:23][CH2:22]2)[NH:8][C:9](=[O:19])[C:10]=1[C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[CH3:18])[CH3:2]

Participants

6

Reactant 3

HCID 67717TrifluoroacetamideHCID 76724Iodobenzene diacetateHCID 68353077HCID 68353077, compound

Product 1

HCID 86707844HCID 86707844, compound

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of carbonic acid 4-(2,5-dimethyl-phenyl)-5-oxo-2-(1-oxo-hexahydro-1λ4-thiopyran-4-ylmethyl)-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester (191 mg, 0.47 mmol), trifluoro-acetamide (104 mg, 0.92 mmol), (diacetoxyiodo)benzene (246 mg, 0.76 mmol), MgO (75 mg, 1.8 mmol) and rhodium acetate (10 mg, 0.023 mmol) in 10 ml of CH2Cl2 was stirred at room temperature for 2 h. Then, it was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography on silica gel. Yield: 80 mg of carbonic acid 4-(2,5-dimethyl-phenyl)-5-oxo-2-[1-oxo-1-(2,2,2-trifluoro-acetylimino)-hexahydro-1λ6-thiopyran-4-ylmethyl]-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester (isomer A, compound P1.6) as a solid, mp 91-93° C. and 40 mg of carbonic acid 4-(2,5-dimethyl-phenyl)-5-oxo-2-[1-oxo-1-(2,2,2-trifluoro-acetylimino)-hexahydro-1λ6-thiopyran-4-ylmethyl]-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester (isomer B, compound P1.7) as a solid, mp 87-89° C.

Workup

  1. filtrationThen, it was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-25e367b77ec840bab7c6b438525736ed
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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