L-Leucine → HCID 54313620, compound

HRID 1953913Notes

Reaction equation

HRID 1953913 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH:10](=O)[CH2:11][CH:12]([CH3:14])[CH3:13].[OH-].[Na+]>[Pd].C(O)C>[CH3:13][CH:12]([CH2:11][CH3:10])[CH2:14][NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 6106L-LeucineHCID 115523-MethylbutanalHCID 14798Sodium Hydroxide

Product 1

HCID 54313620HCID 54313620, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A vessel containing 100 g of L-Leucine, 1600 mL of ethanol, 8 g of 2% Pd/C, and 131.5 g of isovaleraldehyde was shaken under hydrogen. After the reaction was finished, the ethanol solution was collected by filtration. Then 300 mL of concentrated HCl was added to the Pd/C-compound mixture, and the mixture was filtered again to give the second filtrate. The second filtration provided the product in concentrated HCl, and it was added NaOH to pH 6.5. The product precipitated out as a white solid, and it was collected by filtration. The crude product was washed with water (200 mL) and acetone (300 mL), then it was dried under vacuum to yield N-(2-methylbutyl)-leucine (50 g); mp 275° C. (dec.).

Workup

  1. filtrationthe ethanol solution was collected by filtration
  2. additionThen 300 mL of concentrated HCl was added to the Pd/C-compound mixture
  3. filtrationthe mixture was filtered again
  4. customto give the second filtrate
  5. filtrationThe second filtration
  6. customprovided the product in concentrated HCl
  7. customThe product precipitated out as a white solid, and it
  8. filtrationwas collected by filtration
  9. washThe crude product was washed with water (200 mL) and acetone (300 mL)
  10. customit was dried under vacuum

Sources & evidence

ORD record
ord-e2601fa1eb6f441d9ac7030b65cbd681
Source dataset
uspto-grants-2000_09
Patent number
US06117841

Reaction notes

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