Trifluoroacetic acid → HCID 11401990, compound

HRID 559474Notes

Reaction equation

HRID 559474 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:22][C:19]([F:20])([F:21])[C:16]1[CH:17]=[CH:18][C:13]([N:10]2[CH2:11][CH2:12][C@@H:8]([NH2:7])[CH2:9]2)=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 29945537HCID 29945537, compound

Product 1

HCID 11401990HCID 11401990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of D1 (11.5 g, 0.04 mol) in DCM (80 ml) was cooled (ice-bath) and trifluoroacetic acid (excess, 50 ml) was added. Reaction was warmed to ambient temperature, stirred for 3 h and partitioned between ethyl acetate and aqueous sodium hydroxide. The organic phase was separated, dried (MgSO4) and filtered. Removal of solvent under reduced pressure afforded the crude product as a yellow oil. Bulb to bulb distillation under reduced pressure initially afforded the title compound as an oil which crystallised on standing.

Workup

  1. additionwas added
  2. customReaction
  3. custompartitioned between ethyl acetate and aqueous sodium hydroxide
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customRemoval of solvent under reduced pressure
  8. customafforded the crude product as a yellow oil
  9. distillationBulb to bulb distillation under reduced pressure

Sources & evidence

ORD record
ord-6b558353ed4c4236bb098433e83f75dd
Source dataset
uspto-grants-2011_11
Patent number
US08063078B2

Reaction notes

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