Trifluoroacetic acid → HCID 66636576, compound

HRID 1094017Notes

Reaction equation

HRID 1094017 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[C:12]3=O)[CH2:5][CH2:4][O:3]1.C(O)(C(F)(F)F)=O.[H][H]>C(O)(=O)C.[Pd]>[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12]3)[CH2:5][CH2:4][O:3]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 666366885-[2-(2-Oxo-oxazolidin-3-yl)-ethyl]-1H-indole-2,3-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 66636576HCID 66636576, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of the compound obtained in Step E (7.68 mmoles) in acetic acid (15 ml) there are added TFA (7 ml) and Pd/C 10% (400 mg). The reaction mixture is stirred at 50° C. under 4 bars of hydrogen overnight. The catalyst is filtered off on a bed of Celite and is then washed with acetic acid (20 ml). The filtrate is evaporated to dryness and the residual acetic acid is removed by azeotropic distillation with toluene. The solid obtained is recrystallised from a mixture of EtOH/ethyl ether to yield the title product after drying in vacuo.

Workup

  1. filtrationThe catalyst is filtered off on a bed of Celite
  2. washis then washed with acetic acid (20 ml)
  3. customThe filtrate is evaporated to dryness
  4. customthe residual acetic acid is removed by azeotropic distillation with toluene
  5. customThe solid obtained
  6. customis recrystallised from a mixture of EtOH/ethyl ether

Sources & evidence

ORD record
ord-e26ded5374f34d66a8bdc50008dab677
Source dataset
uspto-grants-2012_03
Patent number
US08133889B2

Reaction notes

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