Trifluoroacetic acid → HCID 58542372, compound

HRID 1951909Notes

Reaction equation

HRID 1951909 reaction equation
FC(F)(F)C(O)=O.ClC1C=CC([C@H]2N3C(SC(C([N:28]4[CH2:49][C@H:48]([F:50])[CH2:47][C@H:29]4[C:30]([N:32]4[CH2:39][C:36]5([CH2:38][CH2:37]5)[N:35]([C:40](=[O:45])[C:41]([F:44])([F:43])[F:42])[CH2:34][C@H:33]4C)=[O:31])=O)=C3C(C)C)=N[C@]2(C2C=NC(Cl)=CC=2)C)=CC=1F>ClCCl>[F:50][C@H:48]1[CH2:49][NH:28][C@H:29]([C:30]([N:32]2[CH2:39][C:36]3([CH2:38][CH2:37]3)[N:35]([C:40](=[O:45])[C:41]([F:44])([F:43])[F:42])[CH2:34][CH2:33]2)=[O:31])[CH2:47]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58542428HCID 58542428, compound

Product 1

HCID 58542372HCID 58542372, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 ml) was added to a dichloromethane (10 ml) solution of the compound (560 mg, 1.32 mmol) obtained in Step 1 above and the resulting mixture was stirred at room temperature for 1 hour. The reaction solvent was concentrated under reduced pressure and then saturated aqueous sodium bicarbonate solution (30 ml) was added, followed by extraction with chloroform three times. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (380 mg, 89%) as a pale yellow solid.

Workup

  1. concentrationThe reaction solvent was concentrated under reduced pressure
  2. additionsaturated aqueous sodium bicarbonate solution (30 ml) was added
  3. extractionfollowed by extraction with chloroform three times
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-76f35fda404b44d899b5c767e268c49b
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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