HCID 53718280, compound → HCID 19072316, compound

HRID 1955654Notes

Reaction equation

HRID 1955654 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3([O:23][CH3:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[C:3]=1[NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3([O:23][CH3:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[C:3]=1[NH:25][C:26](=[O:31])[C:27]([CH3:29])([CH3:28])[CH3:30]

Participants

4

Reactant 1

HCID 53718280HCID 53718280, compound

Product 1

HCID 19072316HCID 19072316, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product from Example 6 (3.0 g) in ethanol, was added 10% palladium on charcoal (300 mg). The reaction mixture was treated with H2 at atmospheric pressure until uptake ceased. On completion, the reaction was filtered and the solvent was removed from the filtrate in vacuo to give a green oil. Traces of remaining catalyst were removed by filtration to give a yellow oil. The oil was precipitated from ethyl acetate/40°-60° petroleum ether to afford the title compound as a white solid, mp 147°-148°C.

Workup

  1. additionThe reaction mixture was treated with H2 at atmospheric pressure until uptake
  2. filtrationOn completion, the reaction was filtered
  3. customthe solvent was removed from the filtrate in vacuo
  4. customto give a green oil
  5. customTraces of remaining catalyst were removed by filtration
  6. customto give a yellow oil
  7. customThe oil was precipitated from ethyl acetate/40°-60° petroleum ether

Sources & evidence

ORD record
ord-c490d99f870942d8a44289f301518942
Source dataset
uspto-grants-1998_07
Patent number
US05776951

Reaction notes

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