Trifluoroacetic acid → HCID 67410757, compound

HRID 1949651Notes

Reaction equation

HRID 1949651 reaction equation
C(OC(=O)[NH:7][CH:8]([C:12]([N:14]1[CH2:18][CH2:17][CH:16]2[N:19]([C:32]3[N:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[CH2:20][CH:21]([C:22]3[C:30]4[C:25](=[CH:26][C:27]([F:31])=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH:15]12)=[O:13])[CH:9]([CH3:11])[CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]([CH:9]([CH3:11])[CH3:10])[C:12]([N:14]1[CH2:18][CH2:17][CH:16]2[N:19]([C:32]3[N:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[CH2:20][CH:21]([C:22]3[C:30]4[C:25](=[CH:26][C:27]([F:31])=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH:15]12)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67410996HCID 67410996, compound

Product 1

HCID 67410757HCID 67410757, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 72 (210 mg, 0.40 mmol) in DCM (10 mL) was added TFA (4 mL) at 0° C. After 90 min, 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 148 mg (87%) of 73 which was used without further purification. Mass spectrum, m/z [423] (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-d10032e6d0ad49608bcc9589d9f6f24f
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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