Trifluoroacetic acid → HCID 21949625, compound

HRID 2215217Notes

Reaction equation

HRID 2215217 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[C:3]([NH:5][CH:6]([C:10](=[O:13])[CH2:11][CH3:12])[CH2:7][CH:8]=[CH2:9])=O.FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[CH2:7]([C:6]1[N:5]=[C:3]([C:2]([CH3:15])([CH3:14])[CH3:1])[O:13][C:10]=1[CH2:11][CH3:12])[CH:8]=[CH2:9]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 21949646HCID 21949646, compound

Product 1

HCID 21949625HCID 21949625, compound

Procedure

2.10 g of the above prepared 2,2-dimethyl-N-(1-propionyl-but-3-enyl)-propionamide (9.94 mmol) were treated with 16.74 ml of trifluoroacetic acid (219 mmol) and 8.29 ml of trifluoroacetic anhydride (6 eq.) and kept for 4 h at 50°, when TLC indicated the disappearance of starting material. The reaction mixture was then poured onto crashed ice/Na2CO3, the aqueous layer (pH ˜8), extracted twice with AcOEt, washed with water, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=95/5) delivered 1.29 g of the title compound as yellowish liquid.

Workup

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

Sources & evidence

ORD record
ord-7350bd9536734ec2bd15a4ee502efc37
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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