Trifluoroacetic acid → HCID 61368903, compound

HRID 1430225Notes

Reaction equation

HRID 1430225 reaction equation
[CH2:1]([N:8](C(OC(C)(C)C)=O)[NH:9][CH2:10][CH2:11][C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89498414HCID 89498414, compound

Product 1

HCID 61368903HCID 61368903, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 65D (3.1 g) in dichloromethane (10 mL) was added TFA (10 mL) and the mixture was stirred overnight. The mixture was concentrated under vacuum and the residue was dissolved in ethyl acetate (300 mL) and washed with 2N aqueous NaOH, water and brine. The combined organic layers were concentrated, and the residue was dissolved in dichloroethane (30 mL) and MnO2 (2.5 g) was added. The mixture was stirred overnight. Filtration and evaporation of the solvent provided the title compound.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate (300 mL)
  3. washwashed with 2N aqueous NaOH, water and brine
  4. concentrationThe combined organic layers were concentrated
  5. dissolutionthe residue was dissolved in dichloroethane (30 mL)
  6. additionMnO2 (2.5 g) was added
  7. stirringThe mixture was stirred overnight
  8. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-c466ff72a8544ac1a39548b4f123f65d
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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