ethyl 2-acetylamino-2-cyano-3-phenyl-5-oxo-5-(4-fluorophenyl)pentanoate

Base Information

• Chemical Name: ethyl 2-acetylamino-2-cyano-3-phenyl-5-oxo-5-(4-fluorophenyl)pentanoate
• CAS No.: 727678-30-0
• Molecular Formula: C₂₂H₂₁FN₂O₄
• Molecular Weight: 396.418

Synonyms:ethyl 2-acetylamino-2-cyano-3-phenyl-5-oxo-5-(4-fluorophenyl)pentanoate

Chemical Property of ethyl 2-acetylamino-2-cyano-3-phenyl-5-oxo-5-(4-fluorophenyl)pentanoate

Chemical Property:

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Technology Process of ethyl 2-acetylamino-2-cyano-3-phenyl-5-oxo-5-(4-fluorophenyl)pentanoate

There total 2 articles about ethyl 2-acetylamino-2-cyano-3-phenyl-5-oxo-5-(4-fluorophenyl)pentanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

(E)-1-(4-fluorophenyl)-3-phenyl-2-propen-1-one (22966-25-2) + ethyl 2-acetamido-2-cyanoacetate (90877-70-6,4977-62-2) → ethyl 2-acetylamino-2-cyano-3-phenyl-5-oxo-5-(4-fluorophenyl)pentanoate (727678-30-0)

Guidance literature:

With sodium t-butanolate; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1055/s-2004-822325

Reference yield:

ethyl cyanoglyoxylate-2-oxime (3849-21-6) → ethyl 2-acetylamino-2-cyano-3-phenyl-5-oxo-5-(4-fluorophenyl)pentanoate (727678-30-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 g / HOAc; Zn / diethyl ether / 1 h

2: 78 percent / t-BuONa / tetrahydrofuran / 0.5 h / 20 °C

With acetic acid; sodium t-butanolate; zinc; In tetrahydrofuran; diethyl ether; 2: Michael addition;

DOI:10.1055/s-2004-822325

Reference yield: 82.0%

ethyl 2-acetylamino-2-cyano-3-phenyl-5-oxo-5-(4-fluorophenyl)pentanoate (727678-30-0) → ethyl 3-acetylamino-3,4-dihydro-4-phenyl-6-(4-fluorophenyl)-2(1H)pyridone-3-carboxylate (727678-49-1)

Guidance literature:

With hydrogenchloride; In acetic acid; at 20 ℃;

DOI:10.1055/s-2004-822325

upstream raw materials:

(E)-1-(4-fluorophenyl)-3-phenyl-2-propen-1-one

ethyl 2-acetamido-2-cyanoacetate

ethyl cyanoglyoxylate-2-oxime

Downstream raw materials:

ethyl 3-acetylamino-3,4-dihydro-4-phenyl-6-(4-fluorophenyl)-2(1H)pyridone-3-carboxylate

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