Anisole → N-(2-benzoylphenyl)tyrosine methyl ester

HRID 1358579Notes

Reaction equation

HRID 1358579 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[NH2:6].[C:16]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C:25]1=O)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(OC)C=CC=CC=1>[Pd].C(N(CC)CC)C>[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[NH:6][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16](=[O:23])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 7519AnisoleHCID 76956Methyl tyrosinate hydrochlorideHCID 2756272-Benzoylcyclohexanone

Product 1

HCID 10667178N-(2-benzoylphenyl)tyrosine methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of tyrosine methyl ester hydrochloride (4.8 g), 2-benzoylcyclohexanone (5.0 g), palladium on carbon (1.0 g, 10%), triethylamine (2.9 ml) and anisole (70 ml) was heated at reflux for 20 hours. The reaction mixture was filtered and the filtrate was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using hexane: ethyl acetate=3:1 as the eluant to afford the title compound (1.83 g, Rf=0.39: thin layer chromatography on a silica gel plate using hexane: ethyl acetate=3:1 as the eluant).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was partitioned between ethyl acetate and water
  5. washThe extract was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-75e3047c14394a13a12f2857ab425ecd
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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