4-(3-{2-[5-(bis-ethylsulfanyl-methyl)-1-(2-nitro-benzoyl)-pyrrolidin-3-ylidene]-acetylamino}-propionylamino)-1-methyl-1H-pyrrole-2-carboxylic acid (3-dimethylamino-propyl)-amide

Base Information

• Chemical Name: 4-(3-{2-[5-(bis-ethylsulfanyl-methyl)-1-(2-nitro-benzoyl)-pyrrolidin-3-ylidene]-acetylamino}-propionylamino)-1-methyl-1H-pyrrole-2-carboxylic acid (3-dimethylamino-propyl)-amide
• CAS No.: 474524-49-7
• Molecular Formula: C₃₂H₄₅N₇O₆S₂
• Molecular Weight: 687.885
• Mol file: 474524-49-7.mol

Synonyms:4-(3-{2-[5-(bis-ethylsulfanyl-methyl)-1-(2-nitro-benzoyl)-pyrrolidin-3-ylidene]-acetylamino}-propionylamino)-1-methyl-1H-pyrrole-2-carboxylic acid (3-dimethylamino-propyl)-amide

Chemical Property of 4-(3-{2-[5-(bis-ethylsulfanyl-methyl)-1-(2-nitro-benzoyl)-pyrrolidin-3-ylidene]-acetylamino}-propionylamino)-1-methyl-1H-pyrrole-2-carboxylic acid (3-dimethylamino-propyl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(3-{2-[5-(bis-ethylsulfanyl-methyl)-1-(2-nitro-benzoyl)-pyrrolidin-3-ylidene]-acetylamino}-propionylamino)-1-methyl-1H-pyrrole-2-carboxylic acid (3-dimethylamino-propyl)-amide

There total 11 articles about 4-(3-{2-[5-(bis-ethylsulfanyl-methyl)-1-(2-nitro-benzoyl)-pyrrolidin-3-ylidene]-acetylamino}-propionylamino)-1-methyl-1H-pyrrole-2-carboxylic acid (3-dimethylamino-propyl)-amide 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: 60.0%

N-[3-(dimethylamino)propyl]-1-methyl-4-nitro-1H-pyrrole-2-carboxamide (65361-30-0) + (E)-3-[2-[(5S)-5-[bis(ethylthio)methyl]-1-(2-nitrobenzoyl)-tetrahydro-1H-3-pyrrolyliden]-acetamido]propionic acid (474524-48-6) → 4-(3-{2-[5-(bis-ethylsulfanyl-methyl)-1-(2-nitro-benzoyl)-pyrrolidin-3-ylidene]-acetylamino}-propionylamino)-1-methyl-1H-pyrrole-2-carboxylic acid (3-dimethylamino-propyl)-amide (474524-49-7)

Guidance literature:

N-[3-(dimethylamino)propyl]-1-methyl-4-nitro-1H-pyrrole-2-carboxamide; With hydrogen; palladium on activated charcoal; In methanol; for 2h; under 2585.74 Torr;

(E)-3-[2-[(5S)-5-[bis(ethylthio)methyl]-1-(2-nitrobenzoyl)-tetrahydro-1H-3-pyrrolyliden]-acetamido]propionic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1515/HC.2002.8.2.115

Reference yield:

ortho-nitrobenzoic acid (552-16-9,104810-18-6) → 4-(3-{2-[5-(bis-ethylsulfanyl-methyl)-1-(2-nitro-benzoyl)-pyrrolidin-3-ylidene]-acetylamino}-propionylamino)-1-methyl-1H-pyrrole-2-carboxylic acid (3-dimethylamino-propyl)-amide (474524-49-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: SOCl₂ / benzene

2.1: H₂SO₄

3.1: DIBAL-H

4.1: TMSCl

5.1: 60 percent / Ac₂O-DMSO

6.1: 80 percent / benzene

7.1: 90 percent / 1N NaOH

8.1: 70 percent / EDCI; HOBT; NaHCO₃ / dimethylformamide / 12 h

9.1: 90 percent / 1N NaOH / methanol / 40 - 50 °C

10.1: H₂ / 10 percent Pd/C / methanol / 2 h / 2585.74 Torr

10.2: 60 percent / EDCI; HOBT / dimethylformamide / 12 h / 20 °C

With sodium hydroxide; chloro-trimethyl-silane; thionyl chloride; sulfuric acid; hydrogen; acetic anhydride; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; benzene; 7.1: Wittig reaction;

DOI:10.1515/HC.2002.8.2.115

Reference yield:

2-nitrobenzyl chloride (610-14-0) → 4-(3-{2-[5-(bis-ethylsulfanyl-methyl)-1-(2-nitro-benzoyl)-pyrrolidin-3-ylidene]-acetylamino}-propionylamino)-1-methyl-1H-pyrrole-2-carboxylic acid (3-dimethylamino-propyl)-amide (474524-49-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: H₂SO₄

2.1: DIBAL-H

3.1: TMSCl

4.1: 60 percent / Ac₂O-DMSO

5.1: 80 percent / benzene

6.1: 90 percent / 1N NaOH

7.1: 70 percent / EDCI; HOBT; NaHCO₃ / dimethylformamide / 12 h

8.1: 90 percent / 1N NaOH / methanol / 40 - 50 °C

9.1: H₂ / 10 percent Pd/C / methanol / 2 h / 2585.74 Torr

9.2: 60 percent / EDCI; HOBT / dimethylformamide / 12 h / 20 °C

With sodium hydroxide; chloro-trimethyl-silane; sulfuric acid; hydrogen; acetic anhydride; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; benzene; 6.1: Wittig reaction;

DOI:10.1515/HC.2002.8.2.115

upstream raw materials:

N-[3-(dimethylamino)propyl]-1-methyl-4-nitro-1H-pyrrole-2-carboxamide

(E)-3-[2-[(5S)-5-[bis(ethylthio)methyl]-1-(2-nitrobenzoyl)-tetrahydro-1H-3-pyrrolyliden]-acetamido]propionic acid

ortho-nitrobenzoic acid

2-nitrobenzyl chloride