(2S)-N-{4-[(1'-carboxymethyl)oxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal

Base Information

• Chemical Name: (2S)-N-{4-[(1'-carboxymethyl)oxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal
• CAS No.: 642479-00-3
• Molecular Formula: C₁₉H₂₆N₂O₇S₂
• Molecular Weight: 458.557
• Mol file: 642479-00-3.mol

Synonyms:(2S)-N-{4-[(1'-carboxymethyl)oxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal

Chemical Property of (2S)-N-{4-[(1'-carboxymethyl)oxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-N-{4-[(1'-carboxymethyl)oxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal

There total 2 articles about (2S)-N-{4-[(1'-carboxymethyl)oxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 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: 78.0%

{4-[(S)-2-(Bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-acetic acid methyl ester (642478-99-7) → (2S)-N-{4-[(1'-carboxymethyl)oxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal (642479-00-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal (140647-02-5) → (2S)-N-{4-[(1'-carboxymethyl)oxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal (642479-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / K₂CO₃ / dimethylformamide / 24 h / 20 °C

2: 78 percent / aq. LiOH / methanol; tetrahydrofuran / 12 h / 20 °C

With lithium hydroxide; potassium carbonate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

isobutyl chloroformate (543-27-1) + (2S)-N-{4-[(1'-carboxymethyl)oxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal (642479-00-3) → C24H34N2O9S2

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 5 ℃; for 0.25h;

upstream raw materials:

{4-[(S)-2-(Bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-acetic acid methyl ester

(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal

Downstream raw materials:

N-(8-benzyloxy-7-methoxy-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)-2-{4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-acetamide

N-[(3S,5S)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-2-{4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-acetamide