Acetic Acid → 7-Azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester

HRID 382743Notes

Reaction equation

HRID 382743 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([CH:10]1[C:15](=[O:16])[O:14][C:13]([CH3:18])(C)O[C:11]1=O)=[O:9])=[N+:2]=[N-:3].OCC[C:23]#[N:24].C(=O)=O.[N+:28]([C:31]1[CH:38]=[CH:37][C:34](C=O)=[CH:33][CH:32]=1)([O-:30])=[O:29].N1CCCCC1.C(O)(=O)C>CC(O)C.CCOC(C)=O.CCCCCC>[C:23]([CH2:18][CH2:13][O:14][C:15](=[O:16])[C:10](=[CH:11][C:34]1[CH:37]=[CH:38][C:31]([N+:28]([O-:30])=[O:29])=[CH:32][CH:33]=1)[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])#[N:24]

Participants

10

Reactant 6

HCID 176Acetic AcidHCID 280Carbon DioxideHCID 5414-NitrobenzaldehydeHCID 8011HydracrylonitrileHCID 8082PiperidineHCID 230040735-(5-Azidopentanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 538699817-Azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(5-Azidopentanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was heated with 3-hydroxypropionitrile (2.42 g, 34.0 mmol) at 80° C. until no more CO2 was released. After cooling to room temperature, the mixture was diluted with 150 ml of 2-propanol, and 4-nitrobenzaldehyde (4.60 g, 30.3 mmol), piperidine (130 mg, 1.50 mmol) and acetic acid (90 mg, 1.50 mmol) were added. The mixture was stirred at room temperature for 48 hrs. The product, 7-azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester was obtained as a pale-yellow oil (5.73 g, 51% yield) after chromatography (SiO2, Hexane:AcOEt, 2:1).

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-f892da38daa34250877b95160ee8cd54
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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