2-[N-(benzyloxycarbonyl)-N-methylamino]-N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methylbutanamide → N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methyl-2-(methylamino)butanamide

HRID 1383737Notes

Reaction equation

HRID 1383737 reaction equation
C(O[C:9]([N:11]([CH:13]([CH:31]([CH3:33])[CH3:32])[C:14]([NH:16][CH:17]([CH3:30])[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]>[OH-].[OH-].[Pd+2].CO>[C:26]([C:21]1[CH:20]=[C:19]([CH2:18][CH:17]([NH:16][C:14](=[O:15])[CH:13]([NH:11][CH3:9])[CH:31]([CH3:32])[CH3:33])[CH3:30])[CH:24]=[CH:23][C:22]=1[OH:25])([CH3:27])([CH3:29])[CH3:28]

Participants

5

Reactant 2

HCID 211874312-[N-(benzyloxycarbonyl)-N-methylamino]-N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methylbutanamideHCID 178418361HCID 178418361, compound

Product 1

HCID 21187418N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methyl-2-(methylamino)butanamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of 0.54 g (1.19 mmol) of 2-[N-(benzyloxycarbonyl)-N-methylamino]-N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methylbutanamide and 0.10 g of a 20% palladium hydroxide on carbon catalyst in methanol (8 ml) was stirred in a hydrogen atmosphere for 2 hours. After filtering off the catalyst, the solvent was distilled off under reduced pressure to give N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methyl-2-(methylamino)butanamide in the amount of 0.36 g (95%).

Workup

  1. filtrationAfter filtering off the catalyst
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4a30e6c9ded14c999b3f09c78f994bbb
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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