Cyclohexene → L-Leucine

HRID 1377900Notes

Reaction equation

HRID 1377900 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C1CCCCC=1>CO>[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 8079CyclohexeneHCID 74840Leucine, N-carboxy-, N-benzyl ester, L-

Product 1

HCID 6106L-Leucine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dov-Leu-Dil-OBut (5) was prepared as follows: A solution of Z-Leu-Dil-OBut (3, 2.22 mM) was dissolved in anhydrous methanol (10 mL) and cyclohexene (10 mL) was added in a nitrogen atmosphere. To the solution was added 5% Pd--C (1.15 g) and the mixture was heated at reflux for 6 minutes. The catalyst was removed by filtering through a layer of celite, the solvent removed under reduced pressure, and the residue dried in high vacuum for 2 hours.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 6 minutes
  3. customThe catalyst was removed
  4. filtrationby filtering through a layer of celite
  5. customthe solvent removed under reduced pressure
  6. customthe residue dried in high vacuum for 2 hours

Sources & evidence

ORD record
ord-ede47f3ffab44ecb825ed107fcc9d470
Source dataset
uspto-grants-1997_09
Patent number
US05665860

Reaction notes

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