DL-norvaline → HCID 178440053, compound

HRID 1462217Notes

Reaction equation

HRID 1462217 reaction equation
[N:1](=[C:3]([C:7](=[O:9])[CH3:8])[C:4](=O)[CH3:5])O.[NH2:10][CH:11](C(O)=O)[CH2:12][CH2:13][CH3:14]>C(#N)C>[C:7]([C:3]1[NH:1][C:11]([CH2:12][CH2:13][CH3:14])=[N:10][C:4]=1[CH3:5])(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 824DL-norvalineHCID 178468373HCID 178468373, compound

Product 1

HCID 178440053HCID 178440053, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An acetonitrile (250 ml) mixture of 3-oximino-2, 4-pentanedione (40 g, 0.31 moles) and d,1-norvaline (43.55 g, 0.372 moles) was heated to reflux under nitrogen. After 23.7 h the reaction mixture was allowed to cool, then suction filtered. The residue was washed with acetonitrile and the combined filtrates concentrated in vacuo. After dissolving the resulting oil in ethyl acetate (100 ml), it was washed with three 40 ml portions of 5% aqueous sodium hydroxide solution. The combined organic extracts were dried over anhydrous potassium carbonate and then concentrated in vacuo to give 0.1 moles (43.5% yield based on recovered d,1-norvaline) of 5-acetyl-4-methyl-2-propylimidazole.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen
  3. temperatureto cool
  4. filtrationsuction filtered
  5. washThe residue was washed with acetonitrile
  6. concentrationthe combined filtrates concentrated in vacuo
  7. dissolutionAfter dissolving the resulting oil in ethyl acetate (100 ml)
  8. washit was washed with three 40 ml portions of 5% aqueous sodium hydroxide solution
  9. dry with materialThe combined organic extracts were dried over anhydrous potassium carbonate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-babd9dfe7a424fbba1d709db82730dd4
Source dataset
uspto-grants-1984_07
Patent number
US04459413

Reaction notes

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