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

Base Information

• Chemical Name: 2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic acid
• CAS No.: 1279707-77-5
• Molecular Formula: C₃₁H₂₉N₃O₆
• Molecular Weight: 539.588
• Mol file: 1279707-77-5.mol

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

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

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

There total 14 articles about 2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic acid 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: 82.0%

L-serin (56-45-1,83245-15-2) + (1-benzyl-5-methoxy-1H-indol-3-yl)-(5-methoxy-1H-indol-4-yl)-methanone (1279707-76-4) + acetic anhydride (108-24-7) → 2-acetylamino-3-[4-(1-benzyl-5-methoxy-1H-indole-3-carbonyl)-5-methoxy-1H-indol-3-yl]-propionic acid (1279707-77-5)

Guidance literature:

L-serin; (1-benzyl-5-methoxy-1H-indol-3-yl)-(5-methoxy-1H-indol-4-yl)-methanone; acetic anhydride; With acetic acid; at 80 ℃; for 2h; Inert atmosphere;

With sodium hydroxide; In diethyl ether; water; at 20 ℃; pH=10; Cooling with ice;

With hydrogenchloride; In water; pH=3;

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 (1279707-77-5)

Guidance literature:

Multi-step reaction with 8 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

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 (1279707-77-5)

Guidance literature:

Multi-step reaction with 11 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

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

L-serin

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

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

Refernces