HCID 22279655, compound → HCID 22279706, compound

HRID 2086189Notes

Reaction equation

HRID 2086189 reaction equation
[CH3:1][C:2]1([CH2:8][CH2:9][C:10]2[S:11][CH:12]=[C:13]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:14]=2)[CH2:6][O:5][C:4](=[O:7])[NH:3]1>C(O)C.[Pd]>[CH3:1][C:2]1([CH2:8][CH2:9][C:10]2[S:11][CH:12]=[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:14]=2)[CH2:6][O:5][C:4](=[O:7])[NH:3]1

Participants

4

Reactant 1

HCID 22279655HCID 22279655, compound

Product 1

HCID 22279706HCID 22279706, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Methyl-4-{2-[4-(5-phenylpent-1-ynyl)thiophen-2-yl]}ethyloxazolidin-2-one (174 mg, 0.49 mmol) obtained in Example 25(h) was dissolved in ethanol (9 ml), and 5% palladium-charcoal (90 mg) was added thereto followed by stirring for 4 hours under a hydrogen atmosphere. After the catalyst was filtered out through Celite, the filtrate was evaporated to dryness under reduced pressure. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=1:1) to give the title compound (164 mg, 93% yield).

Workup

  1. filtrationAfter the catalyst was filtered out through Celite
  2. customthe filtrate was evaporated to dryness under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ebc6043ca35f431c902b71cf3dfccebb
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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