2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamide → 3-Methyl-2-methylaminobutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamide

HRID 1988247Notes

Reaction equation

HRID 1988247 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:23][C:24](=[O:41])[CH:25]([N:29](C(OCC2C=CC=CC=2)=O)[CH3:30])[CH:26]([CH3:28])[CH3:27])[C:14](=[O:22])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[C].[Pd]>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:23][C:24](=[O:41])[CH:25]([NH:29][CH3:30])[CH:26]([CH3:27])[CH3:28])[C:14](=[O:22])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 867608942-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamideHCID 178418361HCID 178418361, compound

Product 1

HCID 867608933-Methyl-2-methylaminobutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamideYield 98.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamide (1.74 g, 3.10 mmol) in methanol (50 ml), 10% palladium carbon (300 mg) was added and stirred in a hydrogen atmosphere at room temperature overnight. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The thus obtained residue was subjected to silica gel column chromatography (developing solvent: methanol:aqueous ammonia:methylene chloride=5:0.1:100), giving the titled compound (1.30 g, 98%).

Workup

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

Sources & evidence

ORD record
ord-5b742ff773f04c55bcf9722635948f8c
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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