(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoic acid → O-Methyl-L-Tyrosine

HRID 327791Notes

Reaction equation

HRID 327791 reaction equation
C(OC([NH:11][C@H:12]([C:22]([OH:24])=[O:23])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=O)C1C=CC=CC=1>C(O)C.[Pd].C1CCCCC=1>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C@@H:12]([C:22]([OH:24])=[O:23])[NH2:11])=[CH:19][CH:18]=1

Participants

5

Reactant 1

HCID 10496574(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoic acid

Product 1

HCID 2723935O-Methyl-L-TyrosineYield 43%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

N-Benzyloxycarbonyl-O-methyl-L-tyrosine (5.7 g, 17.3 mmol) was dissolved in ethanol (50 ml) and the solution added to a suspension of 10% palladium on charcoal (100 mg) in cyclohexene (10 ml). The reaction was then heated at reflux for 1 h, allowed to cool to ambient temperature, filtered, and the filtrate concentrated to give O-methyl-L-tyrosine (1.4 g, 43%) as a white solid which was used directly in the next step.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureat reflux for 1 h
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-d83993f241eb470f96ea325a0ead3e70
Source dataset
uspto-grants-1993_12
Patent number
US05274094

Reaction notes

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