HCID 67429355, compound → HCID 86625703, compound

HRID 1662669Notes

Reaction equation

HRID 1662669 reaction equation
C(OC(=O)[N:10]([CH2:18][CH2:19][O:20]CC1C=CC=CC=1)[C@@H:11]([CH3:17])[C:12]([N:14]([CH3:16])[CH3:15])=[O:13])C1C=CC=CC=1.[H][H]>CCO.[Pd]>[OH:20][CH2:19][CH2:18][NH:10][C@@H:11]([CH3:17])[C:12]([N:14]([CH3:16])[CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 67429355HCID 67429355, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86625703HCID 86625703, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

Under nitrogen atmosphere, to a solution of 2.75 g of the compound obtained in Step 79-2 in EtOH (30 ml) was added palladium-activated carbon (10% Pd, 0.30 g), and the inside of the reaction system was displaced with hydrogen gas. The solution was stirred for 24 hours at 45° C., then, the reaction solution was filtered, and the solvent was filtered out under reduced pressure. To a solution of the obtained residue in EtOH (30 ml) solution was added palladium-activated carbon (10% Pd, 0.30 g), and the reaction system was displaced with hydrogen gas, again. The solution was stirred for one day at 45° C., then, the reaction solution was filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: CHCl3/MeOH=9/1 to 4/1; v/v) to obtain 734 mg of the title compound (colorless oil).

Workup

  1. filtrationthe reaction solution was filtered
  2. filtrationthe solvent was filtered out under reduced pressure
  3. additionTo a solution of the obtained residue in EtOH (30 ml) solution was added palladium-activated carbon (10% Pd, 0.30 g)
  4. stirringThe solution was stirred for one day at 45° C.
  5. filtrationthe reaction solution was filtered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: CHCl3/MeOH=9/1 to 4/1; v/v)

Sources & evidence

ORD record
ord-36421ef84bcf4397a2eca8bf46779876
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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