p-nitrobenzyl (5R,6S)-6-bromo-6-[(R)-hydroxy-(2,3-dihydroimidazo[2,1-b]thiazol-6-yl)methyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Base Information

Chemical Name:p-nitrobenzyl (5R,6S)-6-bromo-6-[(R)-hydroxy-(2,3-dihydroimidazo[2,1-b]thiazol-6-yl)methyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
CAS No.:769937-24-8
Molecular Formula:C₁₉H₁₅BrN₄O₆S₂
Molecular Weight:539.387
Hs Code.:

Synonyms:p-nitrobenzyl (5R,6S)-6-bromo-6-[(R)-hydroxy-(2,3-dihydroimidazo[2,1-b]thiazol-6-yl)methyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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Chemical Property of p-nitrobenzyl (5R,6S)-6-bromo-6-[(R)-hydroxy-(2,3-dihydroimidazo[2,1-b]thiazol-6-yl)methyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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Technology Process of p-nitrobenzyl (5R,6S)-6-bromo-6-[(R)-hydroxy-(2,3-dihydroimidazo[2,1-b]thiazol-6-yl)methyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

There total 7 articles about p-nitrobenzyl (5R,6S)-6-bromo-6-[(R)-hydroxy-(2,3-dihydroimidazo[2,1-b]thiazol-6-yl)methyl]-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: 17.0%

: 157459-71-7
2,3-dihydroimidazo[2,1-b]thiazole-6-carboxaldehyde

: 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

: p-nitrobenzyl (5R,6R)-6-bromo-6-[hydroxy-(2,3-dihydroimidazo[2,1-b]thiazol-6-yl)methyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

: 769937-24-8
p-nitrobenzyl (5R,6S)-6-bromo-6-[(R)-hydroxy-(2,3-dihydroimidazo[2,1-b]thiazol-6-yl)methyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

: 623906-15-0
p-nitrobenzyl (5R,6S)-6-bromo-6-[(S)-hydroxy-(2,3-dihydroimidazo[2,1-b]thiazol-6-yl)methyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: 2,3-dihydroimidazo[2,1-b]thiazole-6-carboxaldehyde; With magnesium bromide; In 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 2.5h;
DOI:10.1021/jo049880g

Reference yield:

: 91922-15-5
6-bromopenicillanic acid

: 769937-24-8
p-nitrobenzyl (5R,6S)-6-bromo-6-[(R)-hydroxy-(2,3-dihydroimidazo[2,1-b]thiazol-6-yl)methyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 7.2 g / K₂CO₃ / dimethylformamide / 1 h / 35 - 40 °C

2.1: 768 g / m-CPBA / CH₂Cl₂ / 0.42 h

3.1: 5.67 g / toluene / 1 h / Heating

4.1: triethylamine / toluene / 2 h / 0 °C

4.2: 567 g / Ac₂O; pyridine; Ph₃P / toluene / 1 h / -15 - -10 °C

5.1: O₃/O₂ / ethyl acetate / 1.5 h / -70 °C

5.2: 42 percent / P(OMe)3 / ethyl acetate / 17.75 h

6.1: MgBr₂ / acetonitrile / 0.5 h / 20 °C

6.2: triethylamine / acetonitrile; tetrahydrofuran / 2.5 h / -20 °C

With oxygen; potassium carbonate; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; magnesium bromide; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo049880g

Reference yield:

: 623905-90-8
p-nitrobenzyl 2-[(3S,4R)-3-bromo-4-formylthio-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

: 769937-24-8
p-nitrobenzyl (5R,6S)-6-bromo-6-[(R)-hydroxy-(2,3-dihydroimidazo[2,1-b]thiazol-6-yl)methyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: O₃/O₂ / ethyl acetate / 1.5 h / -70 °C

1.2: 42 percent / P(OMe)3 / ethyl acetate / 17.75 h

2.1: MgBr₂ / acetonitrile / 0.5 h / 20 °C

2.2: triethylamine / acetonitrile; tetrahydrofuran / 2.5 h / -20 °C

With oxygen; ozone; magnesium bromide; In ethyl acetate; acetonitrile;
DOI:10.1021/jo049880g