HCID 59923438, compound → HCID 59923455, compound

HRID 2297721Notes

Reaction equation

HRID 2297721 reaction equation
C([O:8][CH2:9][CH2:10][NH:11][C:12](=[O:35])[N:13]([C@@H:19]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:20]([NH:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])=[O:21])[CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:27][N:25]([CH3:26])[CH2:24][CH2:23][NH:22][C:20](=[O:21])[C@@H:19]([N:13]([CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18])[C:12]([NH:11][CH2:10][CH2:9][OH:8])=[O:35])[CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 1

HCID 59923438HCID 59923438, compound

Product 1

HCID 59923455HCID 59923455, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, 20% palladium hydroxide on carbon (30 mg) is added to a solution of (2S)-2-[3-[2-(benzyloxy)ethyl]-1-isoamylureido]-N-[2-(dimethylamino)ethyl]-3-phenylpropionamide (Compound No. 21-1, 300 mg) in methanol (10 ml). The mixture is stirred under a hydrogen atmosphere for 4.5 hours. Palladium hydroxide on carbon is filtered out with Celite, and the filtrate is concentrated under reduced pressure. The concentrate is dissolved in ethyl acetate. The solution is washed with a 10% aqueous sodium hydrogencarbonate solution, water and saturated brine successively, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting oily matter is purified by silica gel column chromatography to give 167 mg (68%) of the titled compound (Compound No. 22-1).

Workup

  1. filtrationPalladium hydroxide on carbon is filtered out with Celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. dissolutionThe concentrate is dissolved in ethyl acetate
  4. washThe solution is washed with a 10% aqueous sodium hydrogencarbonate solution, water and saturated brine successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oily matter is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e50f01065a524bb68a063f58756d32d7
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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