1H-Indole-1,2-dicarboxylic acid, 5-[[(1,1-dimethylethoxy)carbonyl]amino]-7-(phenylmethoxy)-, 1-(1,1-dimethylethyl) 2-methyl ester

Base Information

• Chemical Name: 1H-Indole-1,2-dicarboxylic acid, 5-[[(1,1-dimethylethoxy)carbonyl]amino]-7-(phenylmethoxy)-, 1-(1,1-dimethylethyl) 2-methyl ester
• CAS No.: 539856-50-3
• Molecular Formula: C27H32N2O7
• Molecular Weight: 496.56
• Mol file: 539856-50-3.mol

Synonyms:

Chemical Property of 1H-Indole-1,2-dicarboxylic acid, 5-[[(1,1-dimethylethoxy)carbonyl]amino]-7-(phenylmethoxy)-, 1-(1,1-dimethylethyl) 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Indole-1,2-dicarboxylic acid, 5-[[(1,1-dimethylethoxy)carbonyl]amino]-7-(phenylmethoxy)-, 1-(1,1-dimethylethyl) 2-methyl ester

There total 18 articles about 1H-Indole-1,2-dicarboxylic acid, 5-[[(1,1-dimethylethoxy)carbonyl]amino]-7-(phenylmethoxy)-, 1-(1,1-dimethylethyl) 2-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: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + methyl 5-amino-7-(benzyloxy)-1-(tert-butoxycarbonyl)indole-2-carboxylate (539856-43-4) → methyl 7-(benzyloxy)-1-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]indole-2-carboxylate (539856-50-3)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 20h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 1-(1,1-dimethylethyl)-2-methyl-5-nitro-6-(phenylmethoxy)-indole-1,2-dicarboxylate (539856-49-0) → methyl 7-(benzyloxy)-1-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]indole-2-carboxylate (539856-50-3)

Guidance literature:

With dmap; ammonium chloride; zinc; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/acs.joc.5b01373

Reference yield:

methyl 7-(benzyloxy)-5-nitro-1H-indole-2-carboxylate (539856-42-3) → methyl 7-(benzyloxy)-1-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]indole-2-carboxylate (539856-50-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C

2: 98 percent / Zn; NH₄Cl / acetone; H₂O / 0.5 h / 25 °C

3: 227 mg / tetrahydrofuran / 10 h / 25 °C

With dmap; ammonium chloride; zinc; In tetrahydrofuran; water; acetone;

DOI:10.1021/ja064228j

upstream raw materials:

di-tert-butyl dicarbonate

methyl 5-amino-7-(benzyloxy)-1-(tert-butoxycarbonyl)indole-2-carboxylate

3-(benzyloxy)-5-nitrobenzaldehyde

3,5-dinitrobenzaldehyde

Downstream raw materials:

methyl 7-(benzyloxy)-4-bromo-1-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]indole-2-carboxylate

1-(1,1-dimethylethyl)-2-methyl 5-[[(1,1-dimethylethoxy)-carbonyl]amino]-4-iodo-7-(phenylmethoxy)indole-1,2-dicarboxylate

methyl (S)-4,7-di-tert-butoxycarbonyl-6-benzyloxy-2-hydroxy-1,2,3,4-tetrahydropyrrolo[3,2-f]quinoline-8-carboxylate

methyl (R)-4,7-di-tert-butoxycarbonyl-6-benzyloxy-2-hydroxy-1,2,3,4-tetrahydropyrrolo[3,2-f]quinoline-8-carboxylate