HCID 54228087, compound → HCID 21705004, compound

HRID 1595531Notes

Reaction equation

HRID 1595531 reaction equation
[C:1]1([S:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][O:19][C:20]3[CH:33]=[CH:32][C:23]([CH:24]=[C:25]4[S:29][C:28](=[O:30])[NH:27][C:26]4=[O:31])=[CH:22][CH:21]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[C:1]1([S:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][O:19][C:20]3[CH:33]=[CH:32][C:23]([CH2:24][CH:25]4[S:29][C:28](=[O:30])[NH:27][C:26]4=[O:31])=[CH:22][CH:21]=3)=[CH:15][CH:16]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 54228087HCID 54228087, compound

Product 1

HCID 21705004HCID 21705004, compoundYield 48.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.5 g (3.1 mmole) 5-(4-[2-(4-(benzenesulfonyloxy)phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione was hydrogenated on 1 g Pd/C (5%) in ethyl acetate and acetic acid (2.5%) at atmospheric pressure for 24 hours. The reaction mixture was filtered through celite and the solvent was evaporated in vacuo. The starting material was not completely consumed, therefore the hydrogenation was restarted twice with Pd/C (10%), followed by purification by chromatography on silica gel using dichloromethane:methanol (95:5) as eluent to give 0.728 g (yield 48.6%) of the desired product.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was evaporated in vacuo
  3. customThe starting material was not completely consumed
  4. customfollowed by purification by chromatography on silica gel

Sources & evidence

ORD record
ord-055211b0b9a54b0e9b77206da911b586
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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