Methyl 3-oxovalerate → HCID 178436943, compound

HRID 1898909Notes

Reaction equation

HRID 1898909 reaction equation
S(O)(O)(=O)=O.[NH2:6][C:7]1[NH:8][CH:9]=[CH:10][N:11]=1.[CH3:12][CH2:13][C:14]([CH2:16][C:17](OC)=[O:18])=O>C(O)(=O)C>[CH2:13]([C:14]1[CH:16]=[C:17]([OH:18])[N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[N:6]=1)[CH3:12]

Participants

4

Reactant 2

HCID 121699Methyl 3-oxovalerateHCID 135136Bis(2-amino-1H-imidazole) sulphate

Product 1

HCID 178436943HCID 178436943, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

20.0 g (151.4 mmol) commercially available (Aldrich) 2-aminoimidazole sulfate and 19.7 g (151.4 mmol) methyl 3-oxo-n-valerate were heated with reflux in 27 ml acetic acid for 7 h. After cooling to room temperature remaining solids were removed by filtration, and the filtrate was diluted with water, neutralized with sodium hydroxide, and extracted with dichloromethane. The organic layer was dried over sodium sulfate, evaporated in vacuo, while the title compound crystallized in colorless crystals, which were filtered with suction, washed with hexane, and dried in vacuo, m.p. 93°-94° C.

Workup

  1. customwere removed by filtration
  2. additionthe filtrate was diluted with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated in vacuo, while the title compound
  6. customcrystallized in colorless crystals, which
  7. filtrationwere filtered with suction
  8. washwashed with hexane
  9. customdried in vacuo, m.p. 93°-94° C.

Sources & evidence

ORD record
ord-eaf03c9fb9eb46cb8472f19cab08a7f1
Source dataset
uspto-grants-1996_11
Patent number
US05571813

Reaction notes

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