2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic acid methyl ester

Base Information

• Chemical Name: 2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic acid methyl ester
• CAS No.: 1279707-78-6
• Molecular Formula: C₃₂H₃₁N₃O₆
• Molecular Weight: 553.615
• Mol file: 1279707-78-6.mol

Synonyms:2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic acid methyl ester

Chemical Property of 2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic acid methyl ester

There total 15 articles about 2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic 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: 88.0%

2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic acid (1279707-77-5) + methyl iodide (74-88-4) → 2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic acid methyl ester (1279707-78-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2011.01.029

Reference yield:

1-(toluene-4-sulfonyl)-1H-indol-5-ol → 2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic acid methyl ester (1279707-78-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: propionic acid / toluene / 24 h / Reflux

2.1: water; dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2 h / 20 °C

5.1: methanol; potassium hydroxide / tetrahydrofuran / 0.5 h / 20 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

7.1: methanol; potassium hydroxide / tetrahydrofuran / 3 h / Reflux

7.2: 20 °C

8.1: acetic acid / 2 h / 80 °C / Inert atmosphere

8.2: 20 °C / pH 10 / Cooling with ice

8.3: pH 3

9.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

With methanol; water; dihydrogen peroxide; potassium carbonate; acetic acid; propionic acid; potassium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2011.01.029

Reference yield:

indol-5-ol (1953-54-4) → 2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic acid methyl ester (1279707-78-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: hydrogenchloride / tetrahydrofuran; water / 2 h / Reflux

3.2: 20 °C

4.1: propionic acid / toluene / 24 h / Reflux

5.1: water; dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2 h / 20 °C

8.1: methanol; potassium hydroxide / tetrahydrofuran / 0.5 h / 20 °C

9.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

10.1: methanol; potassium hydroxide / tetrahydrofuran / 3 h / Reflux

10.2: 20 °C

11.1: acetic acid / 2 h / 80 °C / Inert atmosphere

11.2: 20 °C / pH 10 / Cooling with ice

11.3: pH 3

12.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

With 1H-imidazole; hydrogenchloride; methanol; water; dihydrogen peroxide; sodium hydride; potassium carbonate; acetic acid; propionic acid; potassium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1016/j.tet.2011.01.029

upstream raw materials:

indol-5-ol

5-(tert-butyl-dimethyl-silanyloxy)-1H-indole

(1-benzyl-5-methoxy-1H-indol-3-yl)-[5-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-methanone

(1-benzyl-5-methoxy-1H-indol-3-yl)-(5-methoxy-1H-indol-4-yl)-methanone

Downstream raw materials:

6-(1-benzyl-5-methoxy-1H-indol-3-yl)-7-methoxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid methyl ester

6-[1-benzyl-5-hydroxy-1H-indol-3-yl]-7-hydroxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid

Refernces