HCID 67142036, compound → HCID 67141101, compound

HRID 1864443Notes

Reaction equation

HRID 1864443 reaction equation
C(OC([N:11]1[C@H:15]([C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=3[CH3:31])[CH2:20][CH2:19]2)=[O:17])[CH2:14][N:13]([S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)(=[O:34])=[O:33])[C:12]1=[O:41])=O)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[C:35]1([S:32]([N:13]2[CH2:14][C@@H:15]([C:16]([N:18]3[CH2:19][CH2:20][N:21]([C:24]4[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=4[CH3:31])[CH2:22][CH2:23]3)=[O:17])[NH:11][C:12]2=[O:41])(=[O:34])=[O:33])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 1

HCID 67142036HCID 67142036, compound

Product 1

HCID 67141101HCID 67141101, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(S)-3-Benzenesulfonyl-5-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-2-oxo-imidazolidine-1-carboxylic acid benzyl ester (300 mg) in ethyl acetate (3 mL) were hydrogenated in the presence of 10% Pd/C (28 mg). After removal of the catalyst and evaporation of the solvent, the residue was purified by column chromatography (SiO2, ethyl acetate) to yield (S)-1-benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one (120 mg) as a white solid. MS: 443.4 ([M+H]+)

Workup

  1. customAfter removal of the catalyst and evaporation of the solvent
  2. customthe residue was purified by column chromatography (SiO2, ethyl acetate)

Sources & evidence

ORD record
ord-6fcf2aaa88ab4f24bd669762932b576f
Source dataset
uspto-grants-2009_12
Patent number
US07625902B2

Reaction notes

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