Methane → 5-(3-Amino-4-methyl-benzyl)-2-(tert-butyl-dimethyl-silyl)-imidazole-1-sulfonic acid dimethylamide

HRID 618237Notes

Reaction equation

HRID 618237 reaction equation
[CH3:1][N:2]([CH3:29])[S:3]([N:6]1[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N+:19]([O-])=O)[CH:13]=2)=[CH:9][N:8]=[C:7]1[Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])(=[O:5])=[O:4].C>C(OCC)(=O)C.[Pd]>[CH3:29][N:2]([CH3:1])[S:3]([N:6]1[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([NH2:19])[CH:13]=2)=[CH:9][N:8]=[C:7]1[Si:22]([C:25]([CH3:27])([CH3:26])[CH3:28])([CH3:23])[CH3:24])(=[O:4])=[O:5]

Participants

5

Reactant 2

HCID 297MethaneHCID 539951302-(tert-Butyl-dimethyl-silyl)-5-(4-methyl-3-nitro-benzyl)-imidazole-1-sulfonic acid dimethylamide

Product 1

HCID 543931395-(3-Amino-4-methyl-benzyl)-2-(tert-butyl-dimethyl-silyl)-imidazole-1-sulfonic acid dimethylamideYield 48.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(tert-Butyl-dimethyl-silyl)-5-(4-methyl-3-nitro-benzyl)-imidazole-1-sulfonic acid dimethylamide (2.32 g) was dissolved in 125 ml of ethyl acetate and 0.50 g of 10% palladium over charcoal (Pd/C) was added. The reaction mixture was hydrogenated on a Parr shaker at 44 lb/in2 for 14 hr. The catalyst was removed by filtration and the solvent was evaporated. The residue was purified by silica gel chromatography eluting with ethyl acetate:hexane (1:3), giving 1.05 g of 5-(3-amino-4-methyl-benzyl)-2-(tert-butyl-dimethyl-silyl)-imidazole-1-sulfonic acid dimethylamide as a white solid. ##STR111##

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with ethyl acetate:hexane (1:3)

Sources & evidence

ORD record
ord-f690db96fa2e46669c1547c0f35c6591
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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