DL-norvaline → HCID 178440053, compound

HRID 1075283Notes

Reaction equation

HRID 1075283 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(O)CCC>[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 55.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To 40 g (0.309 moles) of 3-oximino-2,4-pentanedione dissolved in 200 ml of n-butanol was added 39.92 g (0.341 moles) of d,l-norvaline. The resulting mixture was brought to reflux, while stirring rapidly under nitrogen with an oil bath. After 19.3 h the reaction mixture was cooled, and then suction filtered. The residue was washed with ethyl acetate (100 ml) and the combined filtrates concentrated in vacuo. The resulting oil was dissolved in ethyl acetate (200 ml) and extracted with three 50 ml portions of 5% aqueous sodium hydroxide solution. Removal of the solvent in vacuo gave 0.15 moles (55.7% yield based on recovered d,l-norvaline) of 5-acetyl-4-methyl-2-propylimidazole.

Workup

  1. temperatureto reflux
  2. temperatureAfter 19.3 h the reaction mixture was cooled
  3. filtrationsuction filtered
  4. washThe residue was washed with ethyl acetate (100 ml)
  5. concentrationthe combined filtrates concentrated in vacuo
  6. dissolutionThe resulting oil was dissolved in ethyl acetate (200 ml)
  7. extractionextracted with three 50 ml portions of 5% aqueous sodium hydroxide solution
  8. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-1bae31e2f000464f88f0fc0d04c6405d
Source dataset
uspto-grants-1983_07
Patent number
US04395547

Reaction notes

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