tert-Butyl 4-amino-5-{[(1H-benzotriazol-1-yl)oxy]carbonyl}-1-methyl-1H-pyrrole-3-carboxylate

Base Information

• Chemical Name: tert-Butyl 4-amino-5-{[(1H-benzotriazol-1-yl)oxy]carbonyl}-1-methyl-1H-pyrrole-3-carboxylate
• CAS No.: 77716-16-6
• Molecular Formula: C17H19 N5 O4
• Molecular Weight: 357.369
• DSSTox Substance ID: DTXSID30703774
• Wikidata: Q82636031
• Mol file: 77716-16-6.mol

Synonyms:tert-Butyl 4-amino-5-{[(1H-benzotriazol-1-yl)oxy]carbonyl}-1-methyl-1H-pyrrole-3-carboxylate;DTXSID30703774;AKOS030242786;2-O-(benzotriazol-1-yl) 4-O-tert-butyl 3-amino-1-methylpyrrole-2,4-dicarboxylate

Chemical Property of tert-Butyl 4-amino-5-{[(1H-benzotriazol-1-yl)oxy]carbonyl}-1-methyl-1H-pyrrole-3-carboxylate

Chemical Property:

• PSA: 100.27000
• LogP: 2.45880
• Storage Temp.: Store at -15°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 357.14370410
• Heavy Atom Count: 26
• Complexity: 552

Purity/Quality:

99%min ^*data from raw suppliers

4-tert-Butoxycarbonylamino-1-methyl-1H-pyrrole -2-carboxylic acid benzotriazol-1yl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1=CN(C(=C1N)C(=O)ON2C3=CC=CC=C3N=N2)C

Technology Process of tert-Butyl 4-amino-5-{[(1H-benzotriazol-1-yl)oxy]carbonyl}-1-methyl-1H-pyrrole-3-carboxylate

There total 8 articles about tert-Butyl 4-amino-5-{[(1H-benzotriazol-1-yl)oxy]carbonyl}-1-methyl-1H-pyrrole-3-carboxylate 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: 85.0%

4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid (77716-11-1) + benzotriazol-1-ol (2592-95-2) → 4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylic acid benzotriazol-1yl ester (77716-16-6)

Guidance literature:

With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; for 24h;

DOI:10.1021/ja960720z

Reference yield: 85.0%

→ 4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylic acid benzotriazol-1yl ester (77716-16-6)

Guidance literature:

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylic acid benzotriazol-1yl ester (77716-16-6)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. Na₂CO₃ / dioxane / 3 h

2: aq. NaOH / methanol / 6 h / 60 °C

3: 85 percent / DCC / dimethylformamide / 24 h

With sodium hydroxide; sodium carbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja960720z

upstream raw materials:

4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid

benzotriazol-1-ol

di-tert-butyl dicarbonate

methyl 4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrole-2-carboxylate

Downstream raw materials:

methyl 4-<<<4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrole-2-carboxylate

2-{[4-(phenylazo)benzyl]thio}ethyl 6-{1-methyl-4-[1-methyl-4-(1-methyl-4-{1-methyl-4-[1-methyl-4-(tert-butoxycarbonylamino)pyrrole-2-carbonyl]aminopyrrole-2-carbonyl}aminopyrrole-2-carbonyl)aminopyrrole-2-carbonyl]aminopyrrole-2-carbonyl}aminohexanoate

2-{[4-(phenylazo)benzyl]thio}ethyl 6-[1-methyl-4-(1-methyl-4-{1-methyl-4-[1-methyl-4-(tert-butoxycarbonylamino)pyrrole-2-carbonyl]aminopyrrole-2-carbonyl}aminopyrrole-2-carbonyl)aminopyrrole-2-carbonyl]aminohexanoate

6-[(4-{[4-({4-[(4-Amino-1-methyl-1H-pyrrole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carbonyl]-amino}-1-methyl-1H-pyrrole-2-carbonyl)-amino]-hexanoic acid 2-(4-phenylazo-benzylsulfanyl)-ethyl ester

Refernces

• 1、 -. "Complex formation between dsDNA and pyrrole imidazole polyamides". . . Retrieved 2008/06/13.
• 2、 Baird, Eldon E.,Dervan, Peter B.. "Solid phase synthesis of polyamides containing imidazole and pyrrole amino acids". . p. 6141 - 6146. Retrieved 2007/10/03.