Methanol → HCID 178471115, compound

HRID 657169Notes

Reaction equation

HRID 657169 reaction equation
[Na].[CH:2]([CH:4]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]([O:7]CC)=O)=O.[C:17]1(/[CH:23]=[CH:24]/[C:25](=[NH:27])[NH2:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CO>CCO>[OH:7][C:5]1[C:4]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2][N:27]=[C:25](/[CH:24]=[CH:23]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:26]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14668188CinnamimidamideHCID 86635375Diethyl alpha-formylglutarate Sodium Salt

Product 1

HCID 178471115HCID 178471115, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl α-formylglutarate sodium salt (1 g, 4.2 mmol) and (2E)-3-phenyl-2-propenimidamide (0.61 g, 4.2 mmol), prepared in Example 126 (g), were combined in EtOH (20 mL) and MeOH (10 mL) and heated at reflux for 12 h. The solvent was removed and the resulting solid triturated with ether and filtered to give the desired product as a yellow solid (0.75 g, 56%). The mother liquor contained additional product which was not isolated. LCMS (ES+) m/z 299 (MH+).

Workup

  1. temperatureat reflux for 12 h
  2. customThe solvent was removed
  3. customthe resulting solid triturated with ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-acd65e24c48e471eae398574b5eef723
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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