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ChemicalBook--->CAS DataBase List--->62088-13-5

62088-13-5

62088-13-5 Structure

62088-13-5 Structure
IdentificationBack Directory
[Name]

3-(3-CYANO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER
[CAS]

62088-13-5
[Synonyms]

Ethyl (m-cyanobenzoyl)acetate
ETHYL 3-(3-CYANOPHENYL)-3-OXOPROPANOATE
Ethyl 3-(3-Cyanophenyl)-3-oxopropionate
3-Cyano-b-oxo-benzenepropanoic acid ethyl ester
3-(3-Cyanophenyl)-3-oxopropanoic acid ethyl ester
Benzenepropanoic acid, 3-cyano-β-oxo-, ethyl ester
3-(3-CYANO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER
[Molecular Formula]

C12H11NO3
[MDL Number]

MFCD06656737
[MOL File]

62088-13-5.mol
[Molecular Weight]

217.22
Chemical PropertiesBack Directory
[Boiling point ]

338.0±22.0 °C(Predicted)
[density ]

1.19
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[pka]

9.57±0.46(Predicted)
[Appearance]

White to yellow Solid
Hazard InformationBack Directory
[Uses]

Ethyl 3-(3-cyanophenyl)-3-oxopropanoate is used in the synthetic preparation of benzamidine factor Xa inhibitors containing a vicinally-substituted heterocyclic core towards the discovery of novel antithrombotic agents.
[Synthesis]

3-ACETYLBENZONITRILE

6136-68-1

Diethyl carbonate

105-58-8

3-(3-CYANO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER

62088-13-5

Part A. Preparation of ethyl 3-(3-cyanophenyl)-3-oxopropanoate. To a hexane-washed suspension of sodium hydride (1.2 g, 60% mineral oil suspension, 30.3 mmol) in 40 mL of tetrahydrofuran, diethyl carbonate (3.7 mL, 30.3 mmol) and 3-acetylbenzonitrile (2.2 g, 15.2 mmol) were added sequentially. The resulting suspension was stirred at 65 °C for 1 h and then cooled to room temperature. 40 mL of 10% HCl aqueous solution was added and the reaction mixture was diluted with ethyl acetate and layered. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford 3.2 g (96% yield) of ethyl 3-(4-cyanophenyl)-oxopropanoate, which was pure enough to be used directly in subsequent reactions without further purification. Mass spectrum (NH3-Cl) m/z: 218.3 ([M+H]+).

[References]

[1] Journal of Medicinal Chemistry, 2006, vol. 49, # 6, p. 1910 - 1915
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 5, p. 641 - 645
[3] Patent: WO2011/46774, 2011, A1. Location in patent: Page/Page column 16
[4] Patent: EP946528, 2003, B1
[5] Patent: US6187797, 2001, B1
Spectrum DetailBack Directory
[Spectrum Detail]

3-(3-CYANO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER(62088-13-5)1HNMR
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