BzMePhe → N-Methylphenylalanine

HRID 462664

Reaction equation

HRID 462664 reaction equation
[C:1]([N:9](C)[C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C1C=CC=CC=1)=O.[H][H]>C(O)(=O)C.Cl.[C].[Pd]>[NH:9]([CH3:1])[C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 13961832BzMePheHCID 178418361HCID 178418361, compound

Product 1

HCID 6951135N-Methylphenylalanine

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A 12.66 g portion of the BzMePhe was dissolved in 120 ml of acetic acid and 47 ml of HCl, and the solution was subjected to hydrogen catalytic reduction (room temperature, 8 hours) with addition of 5.0 g of 10% palladium-carbon catalyst. After separating off the catalyst by filtration, the filtrate was concentrated in vacuo, and the concentrate was recrystallized from ethanol (50 ml)-ether (500 ml) to give 7.93 g of MePhe, yeild 94.1%. M.p. 225° C.

Workup

  1. customAfter separating off the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customthe concentrate was recrystallized from ethanol (50 ml)-ether (500 ml)

Sources & evidence

ORD record
ord-e4aa716fb75948f583d68188c191dda6
Source dataset
uspto-grants-1985_05
Patent number
US04517180

Linked notes

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