Trifluoroacetamide → HCID 178429266, compound

HRID 2370611Notes

Reaction equation

HRID 2370611 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=[O:4].[O-2].[Mg+2].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.[CH3:25][C:26]1([CH3:66])[N:30]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][S:40][CH2:41][CH2:42][CH2:43][C:44]([F:50])([F:49])[C:45]([F:48])([F:47])[F:46])[C:29](=[O:51])[N:28]([C:52]2[CH:57]=[CH:56][C:55]([N+:58]([O-:60])=[O:59])=[C:54]([C:61]([F:64])([F:63])[F:62])[CH:53]=2)[C:27]1=[O:65]>C(Cl)Cl.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH3:25][C:26]1([CH3:66])[N:30]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][S:40]([CH2:41][CH2:42][CH2:43][C:44]([F:49])([F:50])[C:45]([F:48])([F:47])[F:46])=[N:5][C:3](=[O:4])[C:2]([F:7])([F:6])[F:1])[C:29](=[O:51])[N:28]([C:52]2[CH:57]=[CH:56][C:55]([N+:58]([O-:60])=[O:59])=[C:54]([C:61]([F:63])([F:64])[F:62])[CH:53]=2)[C:27]1=[O:65]

Participants

7

Reactant 4

HCID 67717TrifluoroacetamideHCID 6850729Magnesium monoxideHCID 12217721Iodo benzene diacetateHCID 46947722HCID 46947722, compound

Product 1

HCID 178429266HCID 178429266, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

2,2,2-trifluoroacetamide (106 mg, 0.94 mmole), magnesium oxide (76 mg, 4 eq.), rhodium acetate in the dimer form (5.2 mg, 0.025 eq.) and iodobenzene diacetate (228 mg, 1.5 eq.) are added at 23° C. to a solution of Example 1 (300 mg, 0.48 mmole) in anhydrous CH2Cl2 (5 ml). Stirring is maintained for 6 hours at 23° C. then the reaction mixture is filtered under vacuum. The filtrate is poured into water (25 ml) and extracted with AcOEt (2×25 ml). The organic phases are combined and washed successively with water (25 ml) and salt water (25 ml). After drying over Na2SO4, the organic solution is filtered and concentrated under vacuum. The evaporation residue is purified on a silica column (eluent: Heptane/AcOEt:5/5 to 3/7). After collection and concentration of the pure fractions, the expected compound is obtained in the form of a colourless oil with a yield of 34% (77 mg).

Workup

  1. filtrationthe reaction mixture is filtered under vacuum
  2. additionThe filtrate is poured into water (25 ml)
  3. extractionextracted with AcOEt (2×25 ml)
  4. washwashed successively with water (25 ml) and salt water (25 ml)
  5. dry with materialAfter drying over Na2SO4
  6. filtrationthe organic solution is filtered
  7. concentrationconcentrated under vacuum
  8. customThe evaporation residue is purified on a silica column (eluent: Heptane/AcOEt:5/5 to 3/7)
  9. customAfter collection and concentration of the pure fractions

Sources & evidence

ORD record
ord-53ba4ac874494085a198bb939f594932
Source dataset
uspto-grants-2014_04
Patent number
US08710091B2

Reaction notes

Loading…