Benzyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate

Base Information

• Chemical Name: Benzyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate
• CAS No.: 77716-20-2
• Molecular Formula: C₂₆H₂₆N₆O₅
• Molecular Weight: 502.53
• Mol file: 77716-20-2.mol

Synonyms:Benzyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate

Chemical Property of Benzyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate

There total 16 articles about Benzyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-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: 59.0%

Benzyl 4-<<(4-Amino-1-methylpyrrol-2-yl)carbonyl>amino>-1-methylpyrrole-2-carboxylate (77716-19-9) + 4-formamido-1-methylimidazole-2-carboxylic acid (77716-18-8) → Benzyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate (77716-20-2)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1002/jps.2600781106

Reference yield:

4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid (77716-11-1) → Benzyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate (77716-20-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) aq. Cs₂CO₂ / 1) H₂O, EtOH; 2) DMF, 40 deg C, overnight

2: TFA / CH₂Cl₂ / 1 h

3: 1.) dicyclohexylcarbodiimide, HOBt, 2.) TEA / 1) CH₂Cl₂, 1 h; 2) CH₂Cl₂, 2 h, 0 deg C, 20 deg C (15 h)

4: 95 percent / H₂ / Pd/C / ethanol / 12 h

5: 59 percent / TFA, EDC / dimethylformamide / Ambient temperature

With TEA; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/jps.2600781106

Reference yield:

ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate (2853-29-4) → Benzyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate (77716-20-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 69 percent / 2 M NaOH / ethanol / 1.5 h / Heating

2: H₂, 1.0 M Na₂CO₃(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature

3: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature

4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C

5: TFA / CH₂Cl₂

6: EDC / dimethylformamide / 40 °C

With sodium hydroxide; hydrogen; sodium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00330a022

upstream raw materials:

Benzyl 4-<<(4-Amino-1-methylpyrrol-2-yl)carbonyl>amino>-1-methylpyrrole-2-carboxylate

4-formamido-1-methylimidazole-2-carboxylic acid

1-Methyl-2-pyrrolecarboxylic acid

methyl N-methylpyrrole-2-carboxylate

Downstream raw materials:

distamycin A hydrochloride