(5R)-6-{acetoxy-[1-(4-nitrobenzyloxycarbonyl)-2-thiazol-2-yl-1H-imidazol-4-yl]methyl}-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

Base Information

• Chemical Name: (5R)-6-{acetoxy-[1-(4-nitrobenzyloxycarbonyl)-2-thiazol-2-yl-1H-imidazol-4-yl]methyl}-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester
• CAS No.: 623906-09-2
• Molecular Formula: C₃₀H₂₁BrN₆O₁₁S₂
• Molecular Weight: 785.566
• Mol file: 623906-09-2.mol

Synonyms:(5R)-6-{acetoxy-[1-(4-nitrobenzyloxycarbonyl)-2-thiazol-2-yl-1H-imidazol-4-yl]methyl}-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

Chemical Property of (5R)-6-{acetoxy-[1-(4-nitrobenzyloxycarbonyl)-2-thiazol-2-yl-1H-imidazol-4-yl]methyl}-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-6-{acetoxy-[1-(4-nitrobenzyloxycarbonyl)-2-thiazol-2-yl-1H-imidazol-4-yl]methyl}-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

There total 5 articles about (5R)-6-{acetoxy-[1-(4-nitrobenzyloxycarbonyl)-2-thiazol-2-yl-1H-imidazol-4-yl]methyl}-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester 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:

acetic anhydride (108-24-7) + (5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester (623564-16-9) + 4-formyl-2-thiazol-2-ylimidazole-1-carboxylic acid 4-nitrobenzyl ester (623906-08-1) → (5R)-6-{acetoxy-[1-(4-nitrobenzyloxycarbonyl)-2-thiazol-2-yl-1H-imidazol-4-yl]methyl}-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester (623906-09-2)

Guidance literature:

(5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester; 4-formyl-2-thiazol-2-ylimidazole-1-carboxylic acid 4-nitrobenzyl ester; With triethylamine; magnesium bromide; In tetrahydrofuran; acetonitrile; at -20 - 20 ℃; for 2.8h; Darkness;

acetic anhydride; With dmap; In tetrahydrofuran; acetonitrile; at 0 ℃; for 20h;

Reference yield:

acetic anhydride (108-24-7) + 6-bromo-6-{hydroxy-[1-(4-nitro-benzyloxycarbonyl)-2-thiazol-2-yl-1H-imidazol-4-yl]-methyl}-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester → (5R)-6-{acetoxy-[1-(4-nitrobenzyloxycarbonyl)-2-thiazol-2-yl-1H-imidazol-4-yl]methyl}-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester (623906-09-2)

Guidance literature:

With dmap; In tetrahydrofuran; acetonitrile; at 0 ℃; for 20h;

DOI:10.1016/j.bmc.2004.08.039

Reference yield:

2-thiazol-2-yl-1H-imidazole-4-carbaldehyde (279251-07-9) → (5R)-6-{acetoxy-[1-(4-nitrobenzyloxycarbonyl)-2-thiazol-2-yl-1H-imidazol-4-yl]methyl}-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester (623906-09-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / N,N'-diisopropyl(ethyl)amine / CH₂Cl₂; dioxane / 2 h / 0 °C

2: MgBr₂; triethylamine / acetonitrile; tetrahydrofuran / 4 h / -20 °C

3: 806 mg / 4-dimethylaminopyridine / tetrahydrofuran; acetonitrile / 20 h / 0 °C

With dmap; triethylamine; N-ethyl-N,N-diisopropylamine; magnesium bromide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetonitrile;

DOI:10.1016/j.bmc.2004.08.039

upstream raw materials:

acetic anhydride

2-thiazol-2-yl-1H-imidazole-4-carbaldehyde

4-nitrobenzyl chloroformate

4-formyl-2-thiazol-2-ylimidazole-1-carboxylic acid 4-nitrobenzyl ester