(5R,6S)-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,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester
• CAS No.: 623564-16-9
• Molecular Formula: C13H9BrN2O5S
• Molecular Weight: 385.195
• European Community (EC) Number: 613-015-8
• DSSTox Substance ID: DTXSID201116870
• Nikkaji Number: J2.090.107A
• Mol file: 623564-16-9.mol

Synonyms:(5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester;SCHEMBL679070;BCQLGSCBQKKBIM-CMPLNLGQSA-N;DTXSID201116870;623564-16-9;4-nitrobenzyl (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;(5R, 6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester;(5R, 6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester;(5R, 6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester;(5R, 6S)-6-bromo-7-oxo-4-thia-l-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester;(5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester;(5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester;(5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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

Chemical Property:

• Vapor Pressure: 4.05E-15mmHg at 25°C
• PSA: 117.73000
• LogP: 2.61910
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 383.94156
• Heavy Atom Count: 22
• Complexity: 541

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1COC(=O)C2=CSC3N2C(=O)C3Br)[N+](=O)[O-]
• Isomeric SMILES: C1=CC(=CC=C1COC(=O)C2=CS[C@H]3N2C(=O)[C@@H]3Br)[N+](=O)[O-]

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

There total 6 articles about (5R,6S)-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: 42.0%

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

Guidance literature:

p-nitrobenzyl 2-[(3S,4R)-3-bromo-4-formylthio-2-oxoazetidin-1-yl]-3-methylbut-2-enoate; With oxygen; ozone; In ethyl acetate; at -70 ℃; for 1.5h;

With phosphorous acid trimethyl ester; In ethyl acetate; for 17.75h;

DOI:10.1021/jo049880g

Reference yield:

6-bromopenicillanic acid (91922-15-5) → (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)

Guidance literature:

Multi-step reaction with 5 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

With oxygen; potassium carbonate; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo049880g

Reference yield:

p-nitrobenzyl 6-bromopenicillanate (100239-31-4) → (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)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 768 g / m-CPBA / CH₂Cl₂ / 0.42 h

2.1: 5.67 g / toluene / 1 h / Heating

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

3.2: 567 g / Ac₂O; pyridine; Ph₃P / toluene / 1 h / -15 - -10 °C

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

4.2: 42 percent / P(OMe)3 / ethyl acetate / 17.75 h

With oxygen; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jo049880g

upstream raw materials:

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

6-bromopenicillanic acid

p-nitrobenzyl 6-bromopenicillanate

6-aminopenicillanic acid

Downstream raw materials:

(5R)-6-[acetoxy-(5,6-dihydro-8H-imidazo[2,1-c][1,4]oxazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid para-nitrobenzyl 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

4-nitrobenzyl-6-[(acetyloxy)-(5-(4-methoxybenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

4-nitrobenzyl-6-[(acetyloxy)-(5-(pyridin-3-ylmethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Refernces

• 1、 -. "PROCESS FOR PREPARING 6-ALKYLIDENE PENEM DERIVATIVES". Page/Page column 49-50. . Retrieved 2010/02/07.