Formamidine acetate → HCID 178494687, compound

HRID 2401213Notes

Reaction equation

HRID 2401213 reaction equation
[CH3:1][CH:2]([C:7](=O)[CH2:8][O:9][CH3:10])[C:3](OC)=[O:4].C(O)(=O)C.[CH:16]([NH2:18])=[NH:17].C[O-].[Na+]>CO>[CH3:1][C:2]1[C:3]([OH:4])=[N:17][CH:16]=[N:18][C:7]=1[CH2:8][O:9][CH3:10]

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 10942334Sodium MethoxideHCID 11084163Methyl 4-methoxy-2-methylacetoacetate2×

Product 1

HCID 178494687HCID 178494687, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of methyl 2-methyl-4-(methyloxy)-3-oxobutanoate (Intermediate 47, 1.01 g, 6.31 mmol) in methanol (7 mL) was added formamidine acetate (0.722 g, 6.94 mmol) and 25% sodium methoxide in MeOH (3.0 mL, 6.31 mmol) and the resulting mixture was heated under reflux for 2 hours, cooled to room temperature and left to stand overnight. The reaction mixture was evaporated under reduced pressure. The residue was diluted with water, adjusted to pH 7 using aqueous 2M HCl solution and extracted with chloroform (×3). The chloroform layers were combined, dried under magnesium sulfate and evaporated under reduced pressure to give the title compound as a white solid (597 mg);

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. waitleft
  4. customThe reaction mixture was evaporated under reduced pressure
  5. additionThe residue was diluted with water
  6. extractionextracted with chloroform (×3)
  7. customdried under magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fe69e65e7bb2454d97f964bcd8afab41
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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