L-Valine → HCID 12837668, compound

HRID 990388Notes

Reaction equation

HRID 990388 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH3:9][C:10](=O)[CH2:11][CH3:12].[H][H]>C(O)C.[Pd]>[CH:10]([NH:1][C@@H:2]([CH:3]([CH3:5])[CH3:4])[C:6]([OH:8])=[O:7])([CH2:11][CH3:12])[CH3:9]

Participants

6

Reactant 3

HCID 6287L-ValineHCID 6569Methyl Ethyl KetoneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 12837668HCID 12837668, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of L-valine (29.29 g, 250 mmol), and 2-butanone (44.8 mL, 500 mmol, Aldrich Inc, Milwaukee, Wis.) was agitated in an atmosphere of hydrogen (pressure, 39-51 psi) at 45° C. in 500 mL ethanol in the presence of Pd/C (20%, 4 g) until the absorption of hydrogen had ceased. The mixture was filtered, and this ethanolic filtrate was set aside, then the filter cake washed with 450 mL 1 M HCl. The ethanolic filtrate was concentrated to dryness and the residue dissolved in the aqueous filtrate above, which was treated with concentrated aqueous sodium hydroxide (29.8%) to adjust the pH to 5.5, and the mixture concentrated to dryness under reduced pressure. The white solid thus obtained was extracted by stirring 2-3 hours vigorously with 250 mL methanol followed by filtration. This process was repeated several times. The combined extracts were concentrated under reduced pressure and the white solid thus obtained was triturated in warm acetone, filtered, and the solids washed with acetone and dried under vacuum to give 23.4 g (54%) of the pure titled compound as a white solid; mp >300° C. APCI-MS m/z 174.2 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake washed with 450 mL 1 M HCl
  3. concentrationThe ethanolic filtrate was concentrated to dryness
  4. dissolutionthe residue dissolved in the aqueous filtrate above, which
  5. additionwas treated with concentrated aqueous sodium hydroxide (29.8%)
  6. concentrationthe mixture concentrated to dryness under reduced pressure
  7. customThe white solid thus obtained
  8. extractionwas extracted
  9. filtrationfollowed by filtration
  10. concentrationThe combined extracts were concentrated under reduced pressure
  11. customthe white solid thus obtained
  12. customwas triturated in warm acetone
  13. filtrationfiltered
  14. washthe solids washed with acetone
  15. customdried under vacuum

Sources & evidence

ORD record
ord-9d54858d59f648d488479561ed793fd4
Source dataset
uspto-grants-2002_10
Patent number
US06458781B1

Reaction notes

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