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

Base Information

• Chemical Name: methyl (E)-3-[2-[(5S)-5-[bis(ethylthio)methyl]-1-(2-nitrobenzoyl)-tetrahydro-1H-3-pyrrolyliden]-acetamido]propionate
• CAS No.: 474524-47-5
• Molecular Formula: C₂₂H₂₉N₃O₆S₂
• Molecular Weight: 495.621
• Mol file: 474524-47-5.mol

Synonyms:methyl (E)-3-[2-[(5S)-5-[bis(ethylthio)methyl]-1-(2-nitrobenzoyl)-tetrahydro-1H-3-pyrrolyliden]-acetamido]propionate

Chemical Property of methyl (E)-3-[2-[(5S)-5-[bis(ethylthio)methyl]-1-(2-nitrobenzoyl)-tetrahydro-1H-3-pyrrolyliden]-acetamido]propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (E)-3-[2-[(5S)-5-[bis(ethylthio)methyl]-1-(2-nitrobenzoyl)-tetrahydro-1H-3-pyrrolyliden]-acetamido]propionate

There total 9 articles about methyl (E)-3-[2-[(5S)-5-[bis(ethylthio)methyl]-1-(2-nitrobenzoyl)-tetrahydro-1H-3-pyrrolyliden]-acetamido]propionate 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: 70.0%

methyl 3-aminopropanoate hydrochloride (3196-73-4) + [(S)-5-(Bis-ethylsulfanyl-methyl)-1-(2-nitro-benzoyl)-pyrrolidin-(3E)-ylidene]-acetic acid (241489-18-9) → methyl (E)-3-[2-[(5S)-5-[bis(ethylthio)methyl]-1-(2-nitrobenzoyl)-tetrahydro-1H-3-pyrrolyliden]-acetamido]propionate (474524-47-5)

Guidance literature:

With sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 12h;

DOI:10.1515/HC.2002.8.2.115

Reference yield:

ortho-nitrobenzoic acid (552-16-9,104810-18-6) → methyl (E)-3-[2-[(5S)-5-[bis(ethylthio)methyl]-1-(2-nitrobenzoyl)-tetrahydro-1H-3-pyrrolyliden]-acetamido]propionate (474524-47-5)

Guidance literature:

Multi-step reaction with 9 steps

1: SOCl₂ / benzene

2: H₂SO₄

3: DIBAL-H

4: TMSCl

5: 60 percent / Ac₂O-DMSO

6: 80 percent / benzene

7: 90 percent / 1N NaOH

8: 70 percent / EDCI; HOBT; NaHCO₃ / dimethylformamide / 12 h

With sodium hydroxide; chloro-trimethyl-silane; thionyl chloride; sulfuric acid; acetic anhydride; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; benzene; 7: Wittig reaction;

DOI:10.1515/HC.2002.8.2.115

Reference yield:

[(S)-5-(Bis-ethylsulfanyl-methyl)-1-(2-nitro-benzoyl)-pyrrolidin-(3E)-ylidene]-acetic acid methyl ester (241489-17-8) → methyl (E)-3-[2-[(5S)-5-[bis(ethylthio)methyl]-1-(2-nitrobenzoyl)-tetrahydro-1H-3-pyrrolyliden]-acetamido]propionate (474524-47-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 1N NaOH

2: 70 percent / EDCI; HOBT; NaHCO₃ / dimethylformamide / 12 h

With sodium hydroxide; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

DOI:10.1515/HC.2002.8.2.115

upstream raw materials:

methyl 3-aminopropanoate hydrochloride

[(S)-5-(Bis-ethylsulfanyl-methyl)-1-(2-nitro-benzoyl)-pyrrolidin-(3E)-ylidene]-acetic acid

ortho-nitrobenzoic acid

2-nitrobenzyl chloride

Downstream raw materials:

C₄₄H₅₇N₁₁O₈S₂

C₃₈H₅₁N₉O₇S₂

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

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