5-(1-(2-(benzyloxycarbonyl-N-methylamino)-3-methylbutyrylamino)-2-(3-tert-butyl-4-hydroxylphenyl)ethyl)imidazolidine-2,4-dione → 5-(1-(3-Methyl-2-methylaminobutyrylamino)-2-(3-tert-butyl-4-hydroxylphenyl)ethyl)imidazolidine-2,4-dione

HRID 1988265Notes

Reaction equation

HRID 1988265 reaction equation
C(O[C:9]([N:11]([CH:13]([CH:37]([CH3:39])[CH3:38])[C:14]([NH:16][CH:17]([CH:30]1[NH:34][C:33](=[O:35])[NH:32][C:31]1=[O:36])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=1)=[O:15])C)=O)C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[CH3:38][CH:37]([CH3:39])[CH:13]([NH:11][CH3:9])[C:14]([NH:16][CH:17]([CH:30]1[NH:34][C:33](=[O:35])[NH:32][C:31]1=[O:36])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=1)=[O:15]

Participants

5

Reactant 2

HCID 178192035-(1-(2-(benzyloxycarbonyl-N-methylamino)-3-methylbutyrylamino)-2-(3-tert-butyl-4-hydroxylphenyl)ethyl)imidazolidine-2,4-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 178191835-(1-(3-Methyl-2-methylaminobutyrylamino)-2-(3-tert-butyl-4-hydroxylphenyl)ethyl)imidazolidine-2,4-dioneYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(1-(2-(benzyloxycarbonyl-N-methylamino)-3-methylbutyrylamino)-2-(3-tert-butyl-4-hydroxylphenyl)ethyl)imidazolidine-2,4-dione (363 mg, 0.675 mmol) in methanol (10 ml), 10% palladium carbon (50 mg) was added and stirred at room temperature in a hydrogen atmosphere overnight. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give the titled compound (261 mg, 96%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a969084750b1405c83d4c49432f634b3
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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