Trifluoroacetic acid → HCID 118274269, compound

HRID 522232Notes

Reaction equation

HRID 522232 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[Br:17])C)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Br:17][C:10]1[CH:11]=[C:12]([F:16])[C:13]([F:15])=[CH:14][C:9]=1[NH:7][CH3:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 121297562HCID 121297562, compound

Product 1

HCID 118274269HCID 118274269, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 144B (29.5 g, 92 mmol) in dichloromethane (200 mL) was added trifluoroacetic acid (141 mL, 1831 mmol). The reaction mixture was stirred at room temperature for 2 hours and concentrated. The residue was partitioned between ethyl acetate and brine. The organic phase was washed with brine, dried with MgSO4, filtered, and concentrated. The filtrate was concentrated and the residue was separated by flash chromatography on silica gel (Teledyne CombiFlash Rf, 40% to 100% ethyl acetate in hexane) to provide the title compound. MS (ESI+) m/z 222 (M+1).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and brine
  3. washThe organic phase was washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationThe filtrate was concentrated
  8. customthe residue was separated by flash chromatography on silica gel (Teledyne CombiFlash Rf, 40% to 100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c8ccef2f93ec4e779f3cc07205b95f24
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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