Trifluoroacetic acid → HCID 67407504, compound

HRID 1949644Notes

Reaction equation

HRID 1949644 reaction equation
C(OC(=O)[NH:7][CH:8]([C:11]([N:13]1[CH2:17][CH2:16][CH:15]2[N:18]([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:19][CH:20]([C:21]3[C:29]4[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=4)[NH:23][CH:22]=3)[CH:14]12)=[O:12])[CH2:9][CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]([CH2:9][CH3:10])[C:11]([N:13]1[CH2:17][CH2:16][CH:15]2[N:18]([S:31]([CH3:34])(=[O:32])=[O:33])[CH2:19][CH:20]([C:21]3[C:29]4[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=4)[NH:23][CH:22]=3)[CH:14]12)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67407303HCID 67407303, compound

Product 1

HCID 67407504HCID 67407504, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 64 (270 mg, 0.53 mmol) in DCM (3 mL) was added TFA (2 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 150 mg (69%) of 65 which was used without further purification. Mass spectrum, m/z [409.2] (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-8c002417335b4d6da370491147505de1
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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