(Z)-4-[Benzoyl-(3-methyl-but-2-enyl)-amino]-4-oxo-but-2-enoic acid ethyl ester

Base Information

• Chemical Name: (Z)-4-[Benzoyl-(3-methyl-but-2-enyl)-amino]-4-oxo-but-2-enoic acid ethyl ester
• CAS No.: 329055-28-9
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.369
• Mol file: 329055-28-9.mol

Synonyms:(Z)-4-[Benzoyl-(3-methyl-but-2-enyl)-amino]-4-oxo-but-2-enoic acid ethyl ester

Chemical Property of (Z)-4-[Benzoyl-(3-methyl-but-2-enyl)-amino]-4-oxo-but-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-4-[Benzoyl-(3-methyl-but-2-enyl)-amino]-4-oxo-but-2-enoic acid ethyl ester

There total 2 articles about (Z)-4-[Benzoyl-(3-methyl-but-2-enyl)-amino]-4-oxo-but-2-enoic acid ethyl ester 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: 76.0%

benzoyl chloride (98-88-4) + (Z)-3-(3-Methyl-but-2-enylcarbamoyl)-acrylic acid ethyl ester (329055-27-8) → (Z)-4-[Benzoyl-(3-methyl-but-2-enyl)-amino]-4-oxo-but-2-enoic acid ethyl ester (329055-28-9)

Guidance literature:

With 4 A molecular sieve; In 1,2-dichloro-ethane; at 60 ℃; for 24h;

DOI:10.1021/ol007009q

Reference yield:

3,3-dimethylallylamine (13822-06-5,108963-90-2) → (Z)-4-[Benzoyl-(3-methyl-but-2-enyl)-amino]-4-oxo-but-2-enoic acid ethyl ester (329055-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diethyl ether / 0.25 h / 0 °C

1.2: 77 percent / SOCl₂ / 4 h / 0 °C

2.1: 76 percent / 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 24 h / 60 °C

With 4 A molecular sieve; In diethyl ether; 1,2-dichloro-ethane;

DOI:10.1021/ol007009q

Reference yield:

(Z)-4-[Benzoyl-(3-methyl-but-2-enyl)-amino]-4-oxo-but-2-enoic acid ethyl ester (329055-28-9) → (-)-kainic acid (487-79-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Mg(ClO₄)2; 2,2-bis[(4R)-phenyl-4,5-dihydrooxazol-2-yl]propane / CH₂Cl₂ / 72 h / 20 °C

1.2: 4 N HCl / ethanol / 2 h / 20 °C

2.1: Cp₂ZrHCl / tetrahydrofuran / 4 h / -30 - 15 °C

2.2: 75 percent / CH₂Cl₂ / 1 h

3.1: 4 N HCl / methanol / 24 h / 20 °C

3.2: 97 percent / KOH / H₂O / 20 h / 20 °C

With hydrogenchloride; Schwartz's reagent; magnesium(II) perchlorate; (4R,4'R)-2,2'-(propane-2,2'diyl)bis(4-phenyl-4,5-dihydrooxazole); In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol007009q

upstream raw materials:

benzoyl chloride

(Z)-3-(3-Methyl-but-2-enylcarbamoyl)-acrylic acid ethyl ester

3,3-dimethylallylamine

Downstream raw materials:

(-)-kainic acid