Ceftobiprole

Base Information

• Chemical Name: Ceftobiprole
• CAS No.: 209467-52-7
• Molecular Formula: C₂₀H₂₂N₈O₆S₂
• Molecular Weight: 534.577
• Mol file: 209467-52-7.mol

Synonyms:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[(2Z)-(5-amino-1,2,4-thiadiazol-3-yl)(hydroxyimino)acetyl]amino]-8-oxo-3-[(E)-[(3'R)-2-oxo[1,3'-bipyrrolidin]-3-ylidene]methyl]-,(6R,7R)- (9CI);BAL 9141;BAL 9141-000;Ceftobiprole;Ro 63-9141;(6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-hydroxyimino-acetyl]amino]-8-oxo-3-[(E)-[2-oxo-1-[(3R)-pyrrolidin-3-yl]pyrrolidin-3-ylidene]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;

Chemical Property of Ceftobiprole

Chemical Property:

• Refractive Index: 1.942
• PKA: 2.46±0.50(Predicted)
• PSA: 256.98000
• Density: 2 g/cm³
• LogP: -0.26550

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ceftobiprole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Broad spectrum antibiotic.
• Clinical Use: Ceftobiprole can be used as Broad spectrum antibiotic and in complicated infections of skin and skin structures.

Technology Process of Ceftobiprole

There total 10 articles about Ceftobiprole 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:

(6R,7R)-7-[(Z)-2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-trityloxyiminoacetylamino]-8-oxo-3-[(E)-(R)-2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (733725-06-9) → ceftobiprole (209467-52-7)

Guidance literature:

(6R,7R)-7-[(Z)-2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-trityloxyiminoacetylamino]-8-oxo-3-[(E)-(R)-2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; With triethylsilane; trifluoroacetic acid; at 0 ℃; for 0.5h;

With sodium hydroxide; In water; pH=3;

Reference yield:

C30H26N6O5PS2(1+)*I(1-) + C8H12N2O2 → ceftobiprole (209467-52-7)

Guidance literature:

With sodium methylate; In methanol; at 25 ℃; for 2h; Time; Concentration;

Reference yield:

2-trityloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)-acetic acid chloride hydrochloride + (6R,7R)-7-amino-3[E-(R)-1'-(5-tert-butyloxycarbonyl)-2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (1256575-34-4) → ceftobiprole (209467-52-7)

Guidance literature:

2-trityloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)-acetic acid chloride hydrochloride; (6R,7R)-7-amino-3[E-(R)-1'-(5-tert-butyloxycarbonyl)-2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; With N,O-bis-(trimethylsilyl)-acetamide; water; N,N-dimethyl-formamide; In dichloromethane;

With triethylsilane; trifluoroacetic acid; In methanol;

upstream raw materials:

(6R,7R)-7-[(Z)-2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-trityloxyiminoacetylamino]-8-oxo-3-[(E)-(R)-2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R,7R)-7-amino-3[E-(R)-1'-(5-tert-butyloxycarbonyl)-2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(1R/S,3'R)-(1'-tert-butyloxycarbonyl-2-oxo-[1,3']bipyrrolidinyl-3-yl)-triphenylphosphonium bromide

ceftobiprole medocaril sodium

Refernces

• 1、 -. "Method for preparing ceftobiprole through one-pot reaction". . . Retrieved 2016/11/17.
• 2、 -. "NEW CRYSTAL POLYMORPHS OF CEFTOBIPROLE". Page/Page column 12. . Retrieved 2010/07/09.