L-Phenylalanine → 3-Cyclohexyl-L-alanine

HRID 1651023Notes

Reaction equation

HRID 1651023 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H]>C(O)(=O)C.[Pt]>[CH2:7]1[CH2:6][CH2:5][CH:4]([CH2:3][C@H:2]([NH2:1])[C:10]([OH:12])=[O:11])[CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 6140L-PhenylalanineHCID 178418361HCID 178418361, compound

Product 1

HCID 7124213-Cyclohexyl-L-alanineYield 106.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

2 g of L-phenylalanine was dissolved in 30 ml of a 50% of acetic acid, and hydrogenated by using 200 mg of platinum as catalyst under elevated pressure (hydrogen pressure: 50 kg/cm2) for 2 hours at a temperature from 40° to 70° C. The catalyst was filtered off and the solvent was distilled off under reduced pressured to obtain 2.2 g of L-cyclohexylalanine as a colorless needle crystal.

Workup

  1. customfor 2 hours
  2. customfrom 40° to 70° C
  3. filtrationThe catalyst was filtered off
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-bf47a6745d174f49b501e1882173468d
Source dataset
uspto-grants-1990_05
Patent number
US04927565

Reaction notes

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