Cefbuperazone

Base Information

• Chemical Name: Cefbuperazone
• CAS No.: 76610-84-9
• Molecular Formula: C₂₂H₂₉N₉O₉S₂
• Molecular Weight: 627.659
• UNII: T0785J3X40
• DSSTox Substance ID: DTXSID701024595
• Nikkaji Number: J34.489C
• Wikipedia: Cefbuperazone
• Wikidata: Q5057221
• NCI Thesaurus Code: C81029
• Metabolomics Workbench ID: 154429
• ChEMBL ID: CHEMBL1908372
• Mol file: 76610-84-9.mol

Synonyms:cefbuperazone;cefbuperazone sodium, (6R-(6alpha,7alpha,7(2R*,3S*)))-isomer;sodium 7beta-(2R, 3S)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-(3-hydroxybutanamido)-7alpha-methoxy-3-((1-methyl-1H-tetrazol-5-yl)thiomethyl)-3-cephem-4-carboxylate;T 1982;T-1982

Chemical Property of Cefbuperazone

Chemical Property:

• Appearance/Colour: Solid
• Melting Point: 118-120 °C
• Refractive Index: 1.778
• PSA: 280.09000
• Density: 1.772 g/cm³
• LogP: -2.23990
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
• XLogP3: -1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 10
• Exact Mass: 627.15296588
• Heavy Atom Count: 42
• Complexity: 1210

Purity/Quality:

98% ^*data from raw suppliers

Cefbuperazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCN(C(=O)C1=O)C(=O)NC(C(C)O)C(=O)NC2(C3N(C2=O)C(=C(CS3)CSC4=NN=NN4C)C(=O)O)OC
• Isomeric SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@]2([C@@H]3N(C2=O)C(=C(CS3)CSC4=NN=NN4C)C(=O)O)OC
• Uses: Cefbuperazone is a second-generation cephalosporin antibiotic.

Technology Process of Cefbuperazone

There total 4 articles about Cefbuperazone 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: 63.3%

→ cefbuperazone (76610-84-9)

Guidance literature:

Reference yield:

(6R,7S)-7-[[(3S)-2-[(4-ethyl-2,3-dioxo-1-piperazinyl)carboxamido]-3-formyloxy-1-oxobutyl]amino]-7-methoxy-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid → cefbupreazone (76610-84-9)

Guidance literature:

With hydrogenchloride; methanol; In water; at 20 - 30 ℃; for 5h;

Reference yield:

2-[(3S)-(4-ethyl-2,3-dioxo-1-piperazinyl)carboxamido]-3-formyloxybutyryl chloride → cefbupreazone (76610-84-9)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / -10 °C

2: 3-methyl-phenol / dichloromethane / 4 h / 30 - 35 °C

3: hydrogenchloride; methanol / water / 5 h / 20 - 30 °C

With hydrogenchloride; methanol; 3-methyl-phenol; triethylamine; In dichloromethane; water;

Refernces

• 1、 -. "7α-methoxycephalosporins and pharmaceutical composition comprising the same". . . Retrieved 2008/06/13.