N-(4-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl)cinnamamide

Base Information

• Chemical Name: N-(4-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl)cinnamamide
• CAS No.: 1513867-91-8
• Molecular Formula: C₁₈H₂₀N₂O₃
• Molecular Weight: 312.368
• Mol file: 1513867-91-8.mol

Synonyms:N-(4-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl)cinnamamide

Chemical Property of N-(4-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl)cinnamamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(4-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl)cinnamamide

There total 9 articles about N-(4-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl)cinnamamide 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: 30.0%

aglairubine → gigantamide A + (E)-N-((E)-4-cinnamoylaminobutyl)-2-methyl-4-oxobut-2-enamide + N-(4-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl)cinnamamide (1513867-91-8)

Guidance literature:

With pyridinium chlorochromate; In chloroform; dimethyl sulfoxide; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.3762/bjoc.10.9

Reference yield:

ethyl 3-acetoxy-4-(4-methoxybenzyloxy)-2-methylenebutanoate → gigantamide A + (E)-N-((E)-4-cinnamoylaminobutyl)-2-methyl-4-oxobut-2-enamide + N-(4-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl)cinnamamide (1513867-91-8)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium tetrahydroborate / tert-butyl alcohol / 19 h / 20 °C

2: water; potassium hydroxide / methanol / 3 h / 20 °C / Inert atmosphere

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / chloroform; tetrahydrofuran / 19 h / 20 °C / Inert atmosphere

4: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere

5: pyridinium chlorochromate / chloroform; dimethyl sulfoxide / 20 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; dimethyl sulfoxide; tert-butyl alcohol;

DOI:10.3762/bjoc.10.9

Reference yield:

(2E)-4-(4-methoxybenzyloxy)-2-methylbut-2-enoic acid ethyl ester (167687-18-5) → gigantamide A + (E)-N-((E)-4-cinnamoylaminobutyl)-2-methyl-4-oxobut-2-enamide + N-(4-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl)cinnamamide (1513867-91-8)

Guidance literature:

Multi-step reaction with 4 steps

1: water; potassium hydroxide / methanol / 3 h / 20 °C / Inert atmosphere

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / chloroform; tetrahydrofuran / 19 h / 20 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere

4: pyridinium chlorochromate / chloroform; dimethyl sulfoxide / 20 h / 20 °C / Inert atmosphere

With water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; dimethyl sulfoxide;

DOI:10.3762/bjoc.10.9

upstream raw materials:

(E)-N-(4-aminobutyl)cinnamamide

(2E)-4-(4-methoxybenzyloxy)-2-methylbut-2-enoic acid ethyl ester

tert-butyl N-[4-(3-phenyl-prop-2-enoylamino)-butyl]carbamate

(E)-3-phenylacrylic acid