Benzyl 4-Amino-1-methylpyrrole-2-carboxylate

Base Information

• Chemical Name: Benzyl 4-Amino-1-methylpyrrole-2-carboxylate
• CAS No.: 77716-14-4
• Molecular Formula: C₁₃H₁₄N₂O₂
• Molecular Weight: 230.266
• Mol file: 77716-14-4.mol

Synonyms:Benzyl 4-Amino-1-methylpyrrole-2-carboxylate

Chemical Property of Benzyl 4-Amino-1-methylpyrrole-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl 4-Amino-1-methylpyrrole-2-carboxylate

There total 12 articles about Benzyl 4-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:

4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid (77716-11-1) → Benzyl 4-Amino-1-methylpyrrole-2-carboxylate (77716-14-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: TFA / CH₂Cl₂ / 1 h

With trifluoroacetic acid; In dichloromethane;

DOI:10.1002/jps.2600781106

Reference yield:

benzyl 4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrole-2-carboxylate (77716-13-3) → Benzyl 4-Amino-1-methylpyrrole-2-carboxylate (77716-14-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1h; Yield given; Ambient temperature; stoppered flask;

DOI:10.1021/jo00330a022

Reference yield:

1-methyl-4-nitro-pyrrol-2-carboxylic acid (13138-78-8) → Benzyl 4-Amino-1-methylpyrrole-2-carboxylate (77716-14-4)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: Cs₂CO₃ / ethanol; H₂O

4: dimethylformamide / 40 °C

5: TFA / CH₂Cl₂ / 1 h / Ambient temperature; stoppered flask

With hydrogen; sodium carbonate; caesium carbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00330a022

upstream raw materials:

benzyl 1-methyl-4-nitropyrrole-2-carboxylate

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

1-Methyl-2-pyrrolecarboxylic acid

methyl N-methylpyrrole-2-carboxylate

Downstream raw materials:

1-Methyl-4-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-1H-pyrrole-2-carboxylic acid benzyl ester

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

(7-tert-Butoxycarbonylamino-5,10-dioxo-5H,10H-dipyrrolo[1,2-a;1',2'-d]pyrazin-2-yl)-carbamic acid tert-butyl ester

4-[(4-tert-Butoxycarbonylamino-1H-pyrrole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid benzyl ester

Refernces

• 1、 Valík, Martin,Dolensky, Bohumil,Pet?í?ková, Hana,Va?ek, Petr,Král, Vladimír. "Novel heterocyclic Tro?ger's base derivatives containing N-methylpyrrole units". . p. 2083 - 2086. Retrieved 2007/10/03.
• 2、 Nishiwaki, Eiji,Nakagawa, Hirofumi,Takasaki, Michika,Matsumoto, Toyomi,Sakurai, Hiromu,Shibuya, Masayuki. "SYNTHESIS OF OLIGO-N-METHYLPYRROLECARBOXAMIDE DERIVATIVES AND THEIR PHOTOCHEMICAL DNA CLEAVING ACTIVITIES". . p. 1763 - 1767. Retrieved 2007/10/02.