HCID 86760291, compound → HCID 71054124, compound

HRID 719383Notes

Reaction equation

HRID 719383 reaction equation
C([O:8][N:9]1[C:13](=[O:14])[CH2:12][C@@H:11]([NH:15][S:16]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)(=[O:18])=[O:17])[C:10]1=[O:35])C1C=CC=CC=1>CCOC(C)=O.CO.[Pd]>[OH:8][N:9]1[C:13](=[O:14])[CH2:12][C@@H:11]([NH:15][S:16]([N:19]2[CH2:20][CH2:21][N:22]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=3)[CH2:23][CH2:24]2)(=[O:17])=[O:18])[C:10]1=[O:35]

Participants

5

Reactant 1

HCID 86760291HCID 86760291, compound

Product 1

HCID 71054124HCID 71054124, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-(4Trifluoromethyl-phenyl)-piperazine-1-sulfonic acid ((3R)-1-benzyloxy-2,5-dioxo-pyrrolidin-3-yl)-amid (76 mg; 0.15 mmol) was dissolved in EtOAc (5 ml)+MeOH (5 ml). A slurry of 10% Pd/C (35 mg) in MeOH (1 ml) was added under a stream of nitrogen. The mixture was hydrogenated at room temperature at 1 atm. pressure of H2 for 1 h. The reaction mixture was filtered through celite and the filtercake was washed with EtOAc and MeOH. Evaporation of solvent, the crude product was purified by flash chromatograohy through 10 g of Si-60-gel using a gradient of 100% Heptane to 100% (EtOAc+1% AcOH), gradient time=30 min, then isocratic system 100% (EtOAc+1% AcOH) for 15 min. flow=20 ml/min. The fractions containing the product was evaporated and the residue was trituated with Et2O and the resulting colourless solid was dried to give the title compound. Obtained 47 mg (74% yield) of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe filtercake was washed with EtOAc and MeOH
  3. customEvaporation of solvent
  4. customthe crude product was purified by flash chromatograohy through 10 g of Si-60-gel
  5. customto 100% (EtOAc+1% AcOH), gradient time=30 min
  6. waitisocratic system 100% (EtOAc+1% AcOH) for 15 min. flow=20 ml/min
  7. additionThe fractions containing the product
  8. customwas evaporated
  9. customthe resulting colourless solid was dried

Sources & evidence

ORD record
ord-fd378d74fb7941958f0c5b9dd2b124f2
Source dataset
uspto-grants-2006_11
Patent number
US07132434B2

Reaction notes

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