Trifluoroacetic acid → HCID 21949609, compound

HRID 2215255Notes

Reaction equation

HRID 2215255 reaction equation
[C:1]([CH:4]([NH:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])[CH2:5][CH:6]=[CH2:7])(=O)[CH3:2].FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[CH2:5]([C:4]1[N:8]=[C:9]([CH:10]([CH3:11])[CH3:12])[O:13][C:1]=1[CH3:2])[CH:6]=[CH2:7]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 21949598HCID 21949598, compound

Product 1

HCID 21949609HCID 21949609, compoundYield 70.6%

Procedure

6.63 g of the above prepared N-(1-acetyl-but-3-enyl)-isobutyramide(33.61 mmol) were treated with 37 ml of trifluoroacetic acid (483 mmol) and 28.03 ml of trifluoroacetic anhydride (6 eq.) and kept for 3 h at 40°, when TLC indicated the disappearance of starting material. The reaction mixture was then poured onto crashed ice/NaHCO3, the aqueous layer (pH ˜8) extracted twice with AcOEt, washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=92/8) yielded 3.92 g of the title compound as yellowish oil.

Workup

  1. additionThe reaction mixture was then poured
  2. extractionthe aqueous layer (pH ˜8) extracted twice with AcOEt
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-04cb6fc852b2459cab9e64bee9b0ad78
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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