Acetate → HCID 10330159, compound

HRID 1033024Notes

Reaction equation

HRID 1033024 reaction equation
[CH2:1]([CH:5]([C:8](=O)[CH3:9])[CH:6]=O)[CH2:2][CH2:3][CH3:4].[Na].[C:12]([CH2:14][C:15]([NH2:17])=[O:16])#[N:13].C([O-])(=O)C.C(O)(=O)C>O>[C:12]([C:14]1[C:15](=[O:16])[NH:17][C:8]([CH3:9])=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]=1)#[N:13]

Participants

6

Reactant 4

HCID 175AcetateHCID 176Acetic AcidHCID 7898CyanoacetamideHCID 86747807HCID 86747807, compound

Product 1

HCID 10330159HCID 10330159, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

According to the method described in J. Heterocyclic Chem., 24, 351 (1987), a mixture of crude sodium 2-butyl-3-oxobutanal (7.39 g), cyanoacetamide (4.15 g, 39 mmol), aqueous piperidinum acetate (3.5 mL) [prepared from glacial acetic acid (0.85 ml), water (2.0 mL) and piperidine (1.45 ml)] in water (32 mL) was refluxed for 3 hours. Acetic acid (2.5 mL) was cautiously added. After cooling to room temperature and stirring overnight, the precipitated solids were collected by filtration. These residues (2.87 g) was chromatographed on silica gel by gradient elution with 1-3% methanol/ethyl acetate. The appropriate fractions were combined and evaporated. Crystallization from methanol gave 1.01 g of pure product.

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationthe precipitated solids were collected by filtration
  3. customThese residues (2.87 g) was chromatographed on silica gel by gradient elution with 1-3% methanol/ethyl acetate
  4. customevaporated
  5. customCrystallization from methanol

Sources & evidence

ORD record
ord-6123e43c2d8c4b6cb25986030e12d93a
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

Loading…