Acetic Acid → HCID 86586634, compound

HRID 396691Notes

Reaction equation

HRID 396691 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([CH:11]1[C:16](=[O:17])[O:15][C:14]([CH3:19])(C)O[C:12]1=O)=[O:10])=[N+:2]=[N-:3].OCC[C:24]#[N:25].C(=O)=O.[N+:29]([C:32]1[CH:39]=[CH:38][C:35](C=O)=[CH:34][CH:33]=1)([O-:31])=[O:30].N1CCCCC1.C(O)(=O)C>CC(O)C>[C:24]([CH2:19][CH2:14][O:15][C:16](=[O:17])[C:11](=[CH:12][C:35]1[CH:38]=[CH:39][C:32]([N+:29]([O-:31])=[O:30])=[CH:33][CH:34]=1)[C:9](=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])#[N:25]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 280Carbon DioxideHCID 5414-NitrobenzaldehydeHCID 8011HydracrylonitrileHCID 8082PiperidineHCID 23004045HCID 23004045, compound

Product 1

HCID 86586634HCID 86586634, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5-(6-Azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was heated with 3-hydroxypropionitrile (8.90 g, 125 mmol) at 80° C. until no more CO2 was released. The reaction mixture was diluted with 150 ml of 2-propanol and 4-nitrobenzaldehyde (6.30 g, 41.7 mmol), piperidine (178 mg, 2.10 mmol) and acetic acid (125 mg, 2.10 mmol) were added. The mixture was stirred at room temperature for 48 hrs. After the solvent was evaporated, the residue was dissolved into CHCl3 (200 ml), washed with water (150 ml) and brine (150 ml). After drying (Na2SO4) and evaporation of solvent, 8-azido-2-[ (4-nitrophenyl)methylene]-3-oxooctanoic acid 2-cyanoethyl ester was obtained as a brownish oil (17.0 g, 100%).

Workup

  1. additionwere added
  2. customAfter the solvent was evaporated
  3. dissolutionthe residue was dissolved into CHCl3 (200 ml)
  4. washwashed with water (150 ml) and brine (150 ml)
  5. customAfter drying
  6. custom(Na2SO4) and evaporation of solvent

Sources & evidence

ORD record
ord-9ab5db66efd74091a9f27eab82b02adb
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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