HCID 53814568, compound → HCID 54406535, compound

HRID 617598Notes

Reaction equation

HRID 617598 reaction equation
[C:1]([O:4][CH2:5][CH:6]([NH:23][C:24](=[O:26])[CH3:25])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]CC2C=CC=CC=2)=[CH:11][CH:10]=1)(=[O:3])[CH3:2]>C(O)C.[C].[Pd]>[C:1]([O:4][CH2:5][CH:6]([NH:23][C:24](=[O:26])[CH3:25])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 53814568HCID 53814568, compound

Product 1

HCID 54406535HCID 54406535, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-acetamido-4-(4-benzyloxyphenyl)butyl acetate (8.32 g) in ethanol (150 ml), 10% palladium-carbon (1 g) was added and the mixture was stirred, under a hydrogen atmosphere, at room temperature for 8.5 hours. Then, the catalyst was filtered off and the solvent was distilled away under reduced pressure. Ethanol (200 ml) and 10% pallladium-carbon (1 g) were added to the residue and the mixture was further stirred, under a hydrogen atmosphere, at room temperature for 3.5 hours. The catalyst was filtered off from the reaction solution and the solvent was distilled away under reduced pressure. The residue was subjected to silica gel chromatography (eluent; ethyl acetate-hexane=1:4) to give the subject compound (5.80 g).

Workup

  1. filtrationThen, the catalyst was filtered off
  2. distillationthe solvent was distilled away under reduced pressure
  3. additionEthanol (200 ml) and 10% pallladium-carbon (1 g) were added to the residue
  4. stirringthe mixture was further stirred, under a hydrogen atmosphere, at room temperature for 3.5 hours
  5. filtrationThe catalyst was filtered off from the reaction solution
  6. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-8dbfc0df80f34868bd1246860e09a32e
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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