(Z)-2-Acetylamino-3-[4-((E)-3-hydroxy-3-methyl-but-1-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-acrylic acid methyl ester

Base Information

• Chemical Name: (Z)-2-Acetylamino-3-[4-((E)-3-hydroxy-3-methyl-but-1-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-acrylic acid methyl ester
• CAS No.: 108868-38-8
• Molecular Formula: C₂₆H₂₈N₂O₆S
• Molecular Weight: 496.584

Synonyms:(Z)-2-Acetylamino-3-[4-((E)-3-hydroxy-3-methyl-but-1-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-acrylic acid methyl ester

Chemical Property of (Z)-2-Acetylamino-3-[4-((E)-3-hydroxy-3-methyl-but-1-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-acrylic acid methyl ester

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Technology Process of (Z)-2-Acetylamino-3-[4-((E)-3-hydroxy-3-methyl-but-1-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-acrylic acid methyl ester

There total 2 articles about (Z)-2-Acetylamino-3-[4-((E)-3-hydroxy-3-methyl-but-1-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-acrylic acid methyl 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:

Methyl 2-acetamidoacrylate (35356-70-8) → (Z)-2-Acetylamino-3-[4-((E)-3-hydroxy-3-methyl-but-1-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-acrylic acid methyl ester (108868-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / triethylamine / 5percent palladium(II)acetate / acetonitrile / 5 h / Heating

2: 83 percent / tri-o-tolylphosphine, triethylamine / palladium(II)acetate / acetonitrile / 5 h / 100 °C

With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In acetonitrile;

DOI:10.1021/ja00248a032

Reference yield:

4-bromo-3-iodo-1-tosyl-1H-indole (90481-83-7) → (Z)-2-Acetylamino-3-[4-((E)-3-hydroxy-3-methyl-but-1-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-acrylic acid methyl ester (108868-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / triethylamine / 5percent palladium(II)acetate / acetonitrile / 5 h / Heating

2: 83 percent / tri-o-tolylphosphine, triethylamine / palladium(II)acetate / acetonitrile / 5 h / 100 °C

With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In acetonitrile;

DOI:10.1021/ja00248a032

Reference yield: 97.0%

(Z)-2-Acetylamino-3-[4-((E)-3-hydroxy-3-methyl-but-1-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-acrylic acid methyl ester (108868-38-8) → 5-Acetyl-6-(2-methyl-propenyl)-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid methyl ester (108868-39-9)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; for 1h; Heating;

DOI:10.1021/ja00248a032

upstream raw materials:

Methyl 2-acetamidoacrylate

4-bromo-3-iodo-1-tosyl-1H-indole

Downstream raw materials:

5-Acetyl-6-(2-methyl-propenyl)-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid methyl ester

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