HCID 86747152, compound → HCID 178470403, compound

HRID 2255152Notes

Reaction equation

HRID 2255152 reaction equation
[C:1]([CH:3]([NH:9][C:10](=[O:18])[C:11](=[N:16][OH:17])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]>C(O)(=O)C>[NH2:2][C:1]1[N+:16]([O-:17])=[C:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:10](=[O:18])[NH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

3

Reactant 1

HCID 86747152HCID 86747152, compound

Product 1

HCID 178470403HCID 178470403, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

400 Milliliters of acetic acid was added to 35 g of ethyl 2-cyano-2-(α-hydroxyiminoisocaproylamino)acetate. The mixture was subjected to a reaction for 1 hour at 70° C. Acetic acid was removed by evaporation, then the residue was mixed with toluene, and toluene was removed by evaporation. This procedure was repeated several times. The residue was purified by a silica gel column chromatography (eluting solvent: 50% by volume of ethyl acetate-n-hexane), followed by recrystallization from ethanol to obtain 21.3 g of 5-amino-6-ethoxycarbonyl-3-isobutyl-1,2-dihydropyrazin-2-one 4-oxide (Compound B-9) as yellow needle-like crystals having a melting point of 179°-181° C.

Workup

  1. customThe mixture was subjected to a reaction for 1 hour at 70° C
  2. customAcetic acid was removed by evaporation
  3. additionthe residue was mixed with toluene, and toluene
  4. customwas removed by evaporation
  5. customThe residue was purified by a silica gel column chromatography (eluting solvent: 50% by volume of ethyl acetate-n-hexane)
  6. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-940f0a6547f648a2b4f074cc27f695e5
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

Loading…