Water → HCID 178436949, compound

HRID 2401181Notes

Reaction equation

HRID 2401181 reaction equation
C(O)(=O)C.[CH:5]([NH2:7])=[NH:6].O=[C:9]([CH2:15][CH3:16])[CH2:10][C:11](OC)=[O:12].C[O-].[Na+].O>CO.C(O)(=O)C>[CH2:15]([C:9]1[N:7]=[CH:5][N:6]=[C:11]([OH:12])[CH:10]=1)[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 121699Methyl 3-oxovalerateHCID 160693Formamidine acetateHCID 10942334Sodium Methoxide

Product 1

HCID 178436949HCID 178436949, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Formamidine acetate (2.64 g, 25.4 mmol) and methyl 3-oxopentanoate (3.0 g, 23.05 mmol) were added to a mixture of sodium methoxide (2.68 g, 49.6 mmol) in methanol (20 mL) and the resulting mixture was stirred at room temperature under argon for 18 hours. Water (6 mL) and acetic acid (3 mL) were added and the solvent was removed under reduced pressure. The residue was diluted with water and extracted with ethyl acetate (×3). The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated under reduced pressure. The resulting solid was triturated with ethyl acetate, filtered and washed with a small volume of ethyl acetate. The solid was dried under high vacuum at 45° C. for 18 hours to give the title compound as a white solid (932 mg);

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate (×3)
  4. customdried under magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting solid was triturated with ethyl acetate
  7. filtrationfiltered
  8. washwashed with a small volume of ethyl acetate
  9. customThe solid was dried under high vacuum at 45° C. for 18 hours

Sources & evidence

ORD record
ord-2ca6d95d54564dfe85b3e2ebbac88fd1
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

Loading…