HCID 86594511, compound → HCID 86594510, compound

HRID 858206Notes

Reaction equation

HRID 858206 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:9]([C:25]2[N:26]=[CH:27][O:28][CH:29]=2)[O:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([CH:17]=[C:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])[CH2:12]2)=[C:6]([CH3:8])[CH:7]=1>C(OCC)(=O)C.CO.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:9]([C:25]2[N:26]=[CH:27][O:28][CH:29]=2)[O:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])[CH2:12]2)=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 1

HCID 86594511HCID 86594511, compound

Product 1

HCID 86594510HCID 86594510, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.35 g of 5-[1-[cis-3-(5-methyl-2-tolyloxazol-4-ylmethoxy)cyclohexyl]-methylidene]thiazolidine-2,4-dione is dissolved in 12 ml of a solvent mixture of ethyl acetate and methanol (3:1), and 20 mg of palladium-on-carbon are added. The mixture is then hydrogenated at room temperature under a hydrogen pressure of 3 bar for 2 hours. The catalyst is filtered off and the solvent is then removed under reduced pressure and the residue is taken up in acetonitrile. The product can be filtered off, giving 0.3 g of 5-[cis-3-(5-methyl-2-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]thiazolidine-2,4-dione as a white solid. C22H26N2O4S (414.52), MS (ESI): 415 (M+H+).

Workup

  1. additionare added
  2. customis then hydrogenated at room temperature under a hydrogen
  3. customfor 2 hours
  4. filtrationThe catalyst is filtered off
  5. customthe solvent is then removed under reduced pressure
  6. filtrationThe product can be filtered off

Sources & evidence

ORD record
ord-6c9baeaa9ab8416a883d5ff86357e2da
Source dataset
uspto-grants-2006_12
Patent number
US07148246B2

Reaction notes

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