4-nitrobenzyl 6-[(acetyloxy)(7-chloroimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate

Base Information

• Chemical Name: 4-nitrobenzyl 6-[(acetyloxy)(7-chloroimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate
• CAS No.: 623906-26-3
• Molecular Formula: C₂₅H₁₆BrClN₄O₇S₂
• Molecular Weight: 663.914
• Mol file: 623906-26-3.mol

Synonyms:4-nitrobenzyl 6-[(acetyloxy)(7-chloroimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate

Chemical Property of 4-nitrobenzyl 6-[(acetyloxy)(7-chloroimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-nitrobenzyl 6-[(acetyloxy)(7-chloroimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate

There total 4 articles about 4-nitrobenzyl 6-[(acetyloxy)(7-chloroimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate 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: 65.0%

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) + 2-formyl-7-chloroimidazo[2,1-b]benzothiazole (623906-25-2) → 4-nitrobenzyl 6-[(acetyloxy)(7-chloroimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate (623906-26-3)

Guidance literature:

2-formyl-7-chloroimidazo[2,1-b]benzothiazole; With magnesium bromide; In tetrahydrofuran; acetonitrile; at 20 ℃; for 0.5h;

(5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester; With triethylamine; In tetrahydrofuran; acetonitrile; at -20 ℃; for 16h;

acetic anhydride; In tetrahydrofuran; acetonitrile; at -20 - 0 ℃;

DOI:10.1021/jm049680x

Reference yield:

6-chloro-2-aminobenzothiazole (95-24-9) → 4-nitrobenzyl 6-[(acetyloxy)(7-chloroimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate (623906-26-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 60 percent / 1,2-dimethoxy-ethane / 6 h / Heating

2.1: LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

3.1: 2.2 g / MnO₂ / CHCl₃ / 24 h / Heating

4.1: MgBr₂*Et₂O / tetrahydrofuran; acetonitrile / 0.5 h / 20 °C

4.2: Et₃N / tetrahydrofuran; acetonitrile / 16 h / -20 °C

4.3: 65 percent / tetrahydrofuran; acetonitrile / -20 - 0 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; magnesium bromide; In tetrahydrofuran; 1,2-dimethoxyethane; chloroform; acetonitrile;

DOI:10.1021/jm049680x

Reference yield:

ethyl 10-chloro-7-thia-2,5-diazatricyclo[6.4.0.02,6]dodeca-1(8),3,5,9,11-pentaene-4-carboxylate (81022-05-1) → 4-nitrobenzyl 6-[(acetyloxy)(7-chloroimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate (623906-26-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

2.1: 2.2 g / MnO₂ / CHCl₃ / 24 h / Heating

3.1: MgBr₂*Et₂O / tetrahydrofuran; acetonitrile / 0.5 h / 20 °C

3.2: Et₃N / tetrahydrofuran; acetonitrile / 16 h / -20 °C

3.3: 65 percent / tetrahydrofuran; acetonitrile / -20 - 0 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; magnesium bromide; In tetrahydrofuran; chloroform; acetonitrile;

DOI:10.1021/jm049680x

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

2-formyl-7-chloroimidazo[2,1-b]benzothiazole

6-chloro-2-aminobenzothiazole