4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazol-2-yl)]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Base Information

Chemical Name:4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazol-2-yl)]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
CAS No.:623906-28-5
Molecular Formula:C₂₄H₁₉BrN₄O₇S₂
Molecular Weight:619.473
Hs Code.:

4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazol-2-yl)]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Synonyms:4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazol-2-yl)]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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Chemical Property of 4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazol-2-yl)]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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Technology Process of 4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazol-2-yl)]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

There total 5 articles about 4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazol-2-yl)]-6-bromo-7-oxo-4-thia-1-azabicyclo[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: 45.0%

: 108-24-7
acetic anhydride

: 623906-29-6
2-formyl-6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazole

: 623564-16-9
(5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

: 623906-28-5
4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazol-2-yl)]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: 2-formyl-6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazole; 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:

: 694-28-0
2-chlorocyclopentanone

: 623906-28-5
4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazol-2-yl)]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: ethanol; tetrahydrofuran / 16 h / Heating

2.1: 3.0 g / NaOEt; EtOH / 48 h / Heating

3.1: 62 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

4.1: 45 percent / MnO₂ / CHCl₃; methanol / 24 h / Heating

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

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

5.3: 45 percent / tetrahydrofuran; acetonitrile / -20 - 0 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; ethanol; sodium ethanolate; magnesium bromide; In tetrahydrofuran; methanol; ethanol; chloroform; acetonitrile;
DOI:10.1021/jm049680x

Reference yield:

: 53051-97-1
4H,5H,6H-cyclopenta[d][1,3]thiazol-2-amine

: 623906-28-5
4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazol-2-yl)]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 3.0 g / NaOEt; EtOH / 48 h / Heating

2.1: 62 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

3.1: 45 percent / MnO₂ / CHCl₃; methanol / 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: 45 percent / tetrahydrofuran; acetonitrile / -20 - 0 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; ethanol; sodium ethanolate; magnesium bromide; In tetrahydrofuran; methanol; chloroform; acetonitrile;
DOI:10.1021/jm049680x