HCID 131726046, compound → HCID 71054178, compound

HRID 719381Notes

Reaction equation

HRID 719381 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 131726046HCID 131726046, compound

Product 1

HCID 71054178HCID 71054178, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-(4Trifluoromethyl-phenyl)-piperazine-1-sulfonic acid ((3S)-1-benzyloxy-2,5-dioxo-pyrrolidin-3-yl)-amid (67 mg; 0.13 mmol) was dissolved in EtOAc (4 ml) +MeOH (4 ml). A slurry of 10% Pd/C (30 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. The filtrate was evaporated and the crude product were purified twice by flash chromatography on Si-60-gel using EtOAc:Heptane (1:1) as eluent 1 to remove impurities, and EtOAc to elute the product. The fractions containing the product is evaporated and the residue is trituated with Et2O, the resulting colourless solid was dried to give the title compound. Obtained 20 mg (36% yield) of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe filtercake was washed with EtOAc and MeOH
  3. customThe filtrate was evaporated
  4. customthe crude product were purified twice by flash chromatography on Si-60-gel
  5. customto remove impurities, and EtOAc
  6. washto elute the product
  7. additionThe fractions containing the product
  8. customis evaporated
  9. customthe resulting colourless solid was dried

Sources & evidence

ORD record
ord-b47bd665f2094acea7e6e68085abb80d
Source dataset
uspto-grants-2006_11
Patent number
US07132434B2

Reaction notes

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