DL-norvaline → HCID 178458956, compound

HRID 1462222Notes

Reaction equation

HRID 1462222 reaction equation
[N:1](=[C:3]([C:7](=[O:10])[CH2:8][CH3:9])[C:4](=O)[CH3:5])O.[NH2:11][CH:12](C(O)=O)[CH2:13][CH2:14][CH3:15].C(C1NC(CCC)=NC=1C)(=O)C>C(O)CCC>[CH3:5][C:4]1[N:11]=[C:12]([CH2:13][CH2:14][CH3:15])[NH:1][C:3]=1[C:7](=[O:10])[C:8]#[CH:9]

Participants

5

Reactant 3

HCID 824DL-norvalineHCID 178440053HCID 178440053, compoundHCID 178459332HCID 178459332, compound

Product 1

HCID 178458956HCID 178458956, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To 92.4 g (0.646 moles) of 3-oximino-2,4-hexanedione dissolved in 807 ml of n-butanol was added 90.75 g (0.775 moles) of d,l-norvaline. The mixture was refluxed 6.25 h, then cooled and concentrated in vacuo. The residue was taken up in ethyl acetate (500 ml), suction filtered and the filtrate washed with 10% aqueous sodium hydroxide (4×100 ml). Removal of the solvent in vacuo gave 0.29 moles (48% yield based on recovered amino acid) of 4-methyl-5-propinoyl-2-propylimidazole and 5-acetyl-4-methyl-2-propylimidazole (87:13 respectively).

Workup

  1. temperatureThe mixture was refluxed 6.25 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. filtrationsuction filtered
  5. washthe filtrate washed with 10% aqueous sodium hydroxide (4×100 ml)
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-7a3ab20e83754e16b0ea2304103d12e7
Source dataset
uspto-grants-1984_07
Patent number
US04459413

Reaction notes

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