Trifluoroacetic acid → HCID 67410675, compound

HRID 1949642Notes

Reaction equation

HRID 1949642 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]2[N:13]([S:26]([CH3:29])(=[O:28])=[O:27])[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]([S:26]([CH3:29])(=[O:27])=[O:28])[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 67212923HCID 67212923, compound

Product 1

HCID 67410675HCID 67410675, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 62 (2.47 g, 5.83 mmol) in DCM (10 mL) was added TFA (5 mL) at 0° C. After 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 1.8 g (95%) of 63 as a white solid which was used without further purification. Mass spectrum, m/z [324.2] (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-108fb614c4c846aabb8e3f7115138367
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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