Carbon Dioxide → HCID 53896319, compound

HRID 322192Notes

Reaction equation

HRID 322192 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-a2f951c388a74687a95df8ca991b7fdc
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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