Acetic acid (E)-2-acetoxymethyl-4-[3-(2-oxo-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-but-3-enyl ester

Base Information

• Chemical Name: Acetic acid (E)-2-acetoxymethyl-4-[3-(2-oxo-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-but-3-enyl ester
• CAS No.: 181271-36-3
• Molecular Formula: C₂₆H₂₇NO₇S
• Molecular Weight: 497.569

Synonyms:Acetic acid (E)-2-acetoxymethyl-4-[3-(2-oxo-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-but-3-enyl ester

Chemical Property of Acetic acid (E)-2-acetoxymethyl-4-[3-(2-oxo-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-but-3-enyl ester

Chemical Property:

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Technology Process of Acetic acid (E)-2-acetoxymethyl-4-[3-(2-oxo-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-but-3-enyl ester

There total 6 articles about Acetic acid (E)-2-acetoxymethyl-4-[3-(2-oxo-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-but-3-enyl 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: 77.0%

Acetic acid (E)-2-acetoxymethyl-4-[3-(2,2-dimethoxy-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-but-3-enyl ester (181271-35-2) → Acetic acid (E)-2-acetoxymethyl-4-[3-(2-oxo-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-but-3-enyl ester (181271-36-3)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 0 ℃; for 1h;

DOI:10.3987/com-96-7493

Reference yield:

4-bromo-1H-indole (52488-36-5) → Acetic acid (E)-2-acetoxymethyl-4-[3-(2-oxo-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-but-3-enyl ester (181271-36-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 53 percent / POCl₃ / 16 h / y

2: 64 percent / K₂CO₃ / 1,2-dimethoxy-ethane / 20 h / Ambient temperature

3: 72 percent / Pd(OAc)2, tri-o-tolylphosphine, tetrabutylammonium chloride, triethylamine / acetonitrile / 20 h / 110 °C

4: 64 percent / phenyllithium / tetrahydrofuran; diethyl ether; cyclohexane / 1 h / 0 °C

5: 75 percent / HCl / 2 h / Ambient temperature

6: CH₂Cl₂; pyridine / 24 h / Ambient temperature

7: 77 percent / TMSCl, NaI / acetonitrile / 1 h / 0 °C

With hydrogenchloride; palladium diacetate; chloro-trimethyl-silane; tetrabutyl-ammonium chloride; potassium carbonate; phenyllithium; triethylamine; tris-(o-tolyl)phosphine; sodium iodide; trichlorophosphate; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; diethyl ether; dichloromethane; cyclohexane; acetonitrile;

DOI:10.3987/com-96-7493

Reference yield:

4-bromo-1H-indole-3-carbaldehyde (98600-34-1) → Acetic acid (E)-2-acetoxymethyl-4-[3-(2-oxo-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-but-3-enyl ester (181271-36-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 64 percent / K₂CO₃ / 1,2-dimethoxy-ethane / 20 h / Ambient temperature

2: 72 percent / Pd(OAc)2, tri-o-tolylphosphine, tetrabutylammonium chloride, triethylamine / acetonitrile / 20 h / 110 °C

3: 64 percent / phenyllithium / tetrahydrofuran; diethyl ether; cyclohexane / 1 h / 0 °C

4: 75 percent / HCl / 2 h / Ambient temperature

5: CH₂Cl₂; pyridine / 24 h / Ambient temperature

6: 77 percent / TMSCl, NaI / acetonitrile / 1 h / 0 °C

With hydrogenchloride; palladium diacetate; chloro-trimethyl-silane; tetrabutyl-ammonium chloride; potassium carbonate; phenyllithium; triethylamine; tris-(o-tolyl)phosphine; sodium iodide; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; diethyl ether; dichloromethane; cyclohexane; acetonitrile;

DOI:10.3987/com-96-7493

upstream raw materials:

Acetic acid (E)-2-acetoxymethyl-4-[3-(2,2-dimethoxy-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-but-3-enyl ester

4-bromo-1H-indole

4-bromo-1H-indole-3-carbaldehyde

3-Vinyl-1,5-dioxa-spiro[5.5]undecane

Downstream raw materials:

Acetic acid 3-acetoxy-2-[2-(toluene-4-sulfonyl)-8-(toluene-4-sulfonylamino)-8,9-dihydro-2H-2-aza-benzo[cd]azulen-7-yl]-propyl ester

N-[7-(2-Hydroxy-1-hydroxymethyl-ethyl)-8,9-dihydro-2H-2-aza-benzo[cd]azulen-8-yl]-4-methyl-benzenesulfonamide

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