Carbon Dioxide → HCID 53896319, compound

HRID 396687Notes

Reaction equation

HRID 396687 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]([CH:9]1[C:14](=[O:15])[O:13][C:12]([CH3:17])(C)OC1=O)=[O:8])=[N+:2]=[N-:3].OCC[C:22]#[N:23].C(=O)=O>C(Cl)Cl>[C:22]([CH2:17][CH2:12][O:13][C:14](=[O:15])[CH2:9][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])#[N:23]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 8011HydracrylonitrileHCID 23004129HCID 23004129, compound

Product 1

HCID 53896319HCID 53896319, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-Azidobutanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was heated with 3-hydroxypropionitrile (5.25 g, 72.0 mmol) at 80° C. until no more CO2 was released. The reaction mixture was diluted with CH2Cl2 (100 ml), washed with water (100 ml) and brine (100 ml). After drying and evaporation of solvent, the product was purified by chromatography (SiO2, CHCl3:MeOH=95:5), 4-azidobutanoylacetic acid 2-cyanoethyl ester was obtained as a yellowish oil (2.86 g, 53.2%).

Workup

  1. washwashed with water (100 ml) and brine (100 ml)
  2. customAfter drying
  3. customevaporation of solvent
  4. customthe product was purified by chromatography (SiO2, CHCl3:MeOH=95:5)

Sources & evidence

ORD record
ord-f4fb0d7bb719451494240d0477c3d1db
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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