Ethanol → HCID 54285395, compound

HRID 990354Notes

Reaction equation

HRID 990354 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C(=O)[CH2:11][CH:12]([CH3:14])[CH3:13].[H][H].[CH2:18](O)C>[Pd]>[CH2:11]([N:1]([CH3:18])[C@@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([OH:9])=[O:8])[CH:12]([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 6106L-LeucineHCID 115523-MethylbutanalHCID 178418361HCID 178418361, compound2×

Product 1

HCID 54285395HCID 54285395, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of L-leucine (100 g, 0.76 mol) and isovaleraldehyde (132 g, 1.53 mol, Aldrich, Milwaukee, Wis.) was agitated in an atmosphere of hydrogen (pressure, 50 psi) at room temperature in absolute ethanol (1.6 L) in the presence of Pd/C (20%, 8 g) until the absorption of hydrogen almost ceased, filtered. The solid was treated with concentrated aqueous HCl (36.5%) until all the desired product was dissolved in the acidic aqueous solution, the catalyst was then removed by filtration. The filtrate was treated with aqueous NaOH solution (50%) to adjust the pH to 6.5. White solid precipitated out which was isolated via filtration. The white solid was triturated, in succession, with 200 mL of water and 300 mL of acetone. After drying under vacuum. 50.0 g (33%) of the pure titled compound was isolated as a white solid: mp 275° C. (decomposed).

Workup

  1. filtrationfiltered
  2. additionThe solid was treated with concentrated aqueous HCl (36.5%) until all the desired product
  3. dissolutionwas dissolved in the acidic aqueous solution
  4. customthe catalyst was then removed by filtration
  5. additionThe filtrate was treated with aqueous NaOH solution (50%)
  6. customWhite solid precipitated out which
  7. customwas isolated via filtration
  8. customThe white solid was triturated, in succession, with 200 mL of water and 300 mL of acetone
  9. customAfter drying under vacuum

Sources & evidence

ORD record
ord-1d2ba1bd45264b72ac2207dc17cd629c
Source dataset
uspto-grants-2002_10
Patent number
US06458781B1

Reaction notes

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