Anisole → HCID 69870678, compound

HRID 1358567Notes

Reaction equation

HRID 1358567 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[N:19]([CH3:20])[C:18]3[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:17]=3[N:16]=2)=[CH:9][CH:8]=1)[NH2:5].[C:28]([CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][C:37]1=O)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1(OC)C=CC=CC=1>[Pd]>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][C:15]2[N:19]([CH3:20])[C:18]3[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:17]=3[N:16]=2)=[CH:11][CH:12]=1)[NH:5][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:28](=[O:35])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 2756272-BenzoylcyclohexanoneHCID 69871137HCID 69871137, compound

Product 1

HCID 69870678HCID 69870678, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 4-(6-methoxy-1-methyl-1H-benzimidazol-2-ylmethoxy)phenylalanine methyl ester (1.1 g), 2-benzoylcyclohexanone (0.7 g), palladium on carbon (10%, 0.2 g) and anisole (15 ml) was heated at reflux for 21 hours. Insoluble material of the reaction mixture was removed by filtration and the anisole of the filtrate was evaporated under reduced pressure. The residue was chromatographed on a silica gel column using hexane:ethyl acetate=1:2 as the eluant to afford the title compound (0.95 g, Rf=0.51 (thin layer chromatography on silica gel using hexane:ethyl acetate=1:3 as the eluant)).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 21 hours
  3. customInsoluble material of the reaction mixture was removed by filtration
  4. customthe anisole of the filtrate was evaporated under reduced pressure
  5. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-a40310565f9c44d1bbc61c806d277a2a
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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