Trifluoroacetic acid → HCID 178437311, compound

HRID 1931295Notes

Reaction equation

HRID 1931295 reaction equation
[CH2:1]([C:3]1([C:18]([NH:20][C:21]2[CH:25]=[C:24]([O:26][CH:27]([CH3:29])[CH3:28])[N:23](COCC[Si](C)(C)C)[N:22]=2)=[O:19])[CH2:8][CH2:7][CH2:6][N:5]([S:9]([C:12]2[N:13]=[CH:14][N:15]([CH3:17])[CH:16]=2)(=[O:11])=[O:10])[CH2:4]1)[CH3:2].C(O)(C(F)(F)F)=O>>[CH2:1]([C:3]1([C:18]([NH:20][C:21]2[CH:25]=[C:24]([O:26][CH:27]([CH3:28])[CH3:29])[NH:23][N:22]=2)=[O:19])[CH2:8][CH2:7][CH2:6][N:5]([S:9]([C:12]2[N:13]=[CH:14][N:15]([CH3:17])[CH:16]=2)(=[O:11])=[O:10])[CH2:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68428585HCID 68428585, compound

Product 1

HCID 178437311HCID 178437311, compoundYield 50%

Procedure

The compound (83 mg, 0.15 mmol) synthesized in (1), TFA (0.9 mL), and distilled water (0.1 mL) were stirred at room temperature for 2 hours. The reaction mixture was diluted with a saturated sodium hydrogen carbonate aqueous solution, and extracted with ethyl acetate. The organic layer was collected, and washed once with saturated brine. The organic layer was then dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was then purified using silica gel column chromatography to obtain the title compound (32 mg, 50%).

Workup

  1. distillationdistilled water (0.1 mL)
  2. additionThe reaction mixture was diluted with a saturated sodium hydrogen carbonate aqueous solution
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was collected
  5. washwashed once with saturated brine
  6. dry with materialThe organic layer was then dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was then purified

Sources & evidence

ORD record
ord-2fd568598bfb44ae965515ab5150a190
Source dataset
uspto-grants-2012_05
Patent number
US08188280B2

Reaction notes

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