(5R)-6-[acetoxy-(3,1'-dimethyl-3H,1'H-[2,4']biimidazolyl-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-(3,1'-dimethyl-3H,1'H-[2,4']biimidazolyl-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.: 801316-26-7
• Molecular Formula: C₂₄H₂₁BrN₆O₇S
• Molecular Weight: 617.437
• Mol file: 801316-26-7.mol

Synonyms:

Chemical Property of (5R)-6-[acetoxy-(3,1'-dimethyl-3H,1'H-[2,4']biimidazolyl-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-(3,1'-dimethyl-3H,1'H-[2,4']biimidazolyl-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 3 articles about (5R)-6-[acetoxy-(3,1'-dimethyl-3H,1'H-[2,4']biimidazolyl-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) + 6-bromo-6-[(1,1'-dimethyl-1H,1'H-[2,4']biimidazolyl-4-yl)-hydroxy-methyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester → (5R)-6-[acetoxy-(3,1'-dimethyl-3H,1'H-[2,4']biimidazolyl-4-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester (801316-26-7)

Guidance literature:

With dmap; In tetrahydrofuran; acetonitrile; at 0 ℃; for 17h;

DOI:10.1016/j.bmc.2004.08.039

Reference yield:

(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) → (5R)-6-[acetoxy-(3,1'-dimethyl-3H,1'H-[2,4']biimidazolyl-4-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester (801316-26-7)

Guidance literature:

Multi-step reaction with 2 steps

1: MgBr₂; triethylamine / acetonitrile; tetrahydrofuran / 6 h / -20 °C

2: 507.6 mg / 4-dimethylaminopyridine / tetrahydrofuran; acetonitrile / 17 h / 0 °C

With dmap; triethylamine; magnesium bromide; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.bmc.2004.08.039

Reference yield:

3,1'-dimethyl-3H,1'H-[2,4']-biimidazolyl-4-carbaldehyde (623905-98-6) → (5R)-6-[acetoxy-(3,1'-dimethyl-3H,1'H-[2,4']biimidazolyl-4-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester (801316-26-7)

Guidance literature:

Multi-step reaction with 2 steps

1: MgBr₂; triethylamine / acetonitrile; tetrahydrofuran / 6 h / -20 °C

2: 507.6 mg / 4-dimethylaminopyridine / tetrahydrofuran; acetonitrile / 17 h / 0 °C

With dmap; triethylamine; magnesium bromide; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.bmc.2004.08.039

upstream raw materials:

acetic anhydride

(5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

3,1'-dimethyl-3H,1'H-[2,4']-biimidazolyl-4-carbaldehyde