3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid

Base Information

• Chemical Name: 3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid
• CAS No.: 736138-20-8
• Molecular Formula: C₂₉H₂₄ClN₃O₆
• Molecular Weight: 545.979
• Mol file: 736138-20-8.mol

Synonyms:3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid

Chemical Property of 3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid

There total 5 articles about 3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic 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:

methyl 3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate (736138-19-5) → 3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid (736138-20-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; at 25 ℃; for 14h;

DOI:10.1021/ja0472735

Reference yield:

5-methoxy-6-benzyloxyindole-2-carboxylic acid (2495-92-3) → 3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid (736138-20-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / H₂ / Pd/C / methanol / 2 h / 25 °C / 760 Torr

2: EDCI; NaHCO₃ / dimethylformamide / 12 h / 25 °C

3: aq. LiOH / tetrahydrofuran; methanol / 14 h / 25 °C

With lithium hydroxide; hydrogen; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja0472735

Reference yield:

5-methoxy-6-hydroxyindole-2-carboxylic acid (2638-99-5) → 3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid (736138-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: EDCI; NaHCO₃ / dimethylformamide / 12 h / 25 °C

2: aq. LiOH / tetrahydrofuran; methanol / 14 h / 25 °C

With lithium hydroxide; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja0472735

upstream raw materials:

methyl 3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate

5-methoxy-6-hydroxyindole-2-carboxylic acid

5-methoxy-6-benzyloxyindole-2-carboxylic acid

methyl 5-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-(1R)-(chloromethyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate