Trifluoroacetic acid → HCID 67408499, compound

HRID 1949649Notes

Reaction equation

HRID 1949649 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]2[N:13]([C:26]3[N:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH2:14][CH:15]([C:16]3[C:24]4[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[CH:9]12)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:25][C:21]1[CH:20]=[C:19]2[C:24]([C:16]([CH:15]3[CH2:14][N:13]([C:26]4[N:27]=[CH:28][CH:29]=[CH:30][N:31]=4)[CH:10]4[CH2:11][CH2:12][NH:8][CH:9]34)=[CH:17][NH:18]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67407141HCID 67407141, compound

Product 1

HCID 67408499HCID 67408499, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 70 (210 mg, 0.49 mmol) in DCM (10 mL) was added TFA (4 mL) at 0° C. After 2.5 h, the reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc and the resultant organic solution was washed successively with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 150 mg (93%) of 71 which was used without further purification. Mass spectrum, m/z [324] (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe resultant organic solution was washed successively with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1e256a4522894e7199e0aa3fc89d904e
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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