Sodium cefamandole

Base Information

• Chemical Name: Sodium cefamandole
• CAS No.: 30034-03-8
• Molecular Formula: C18H17N6NaO5S2
• Molecular Weight: 484.492
• Mol file: 30034-03-8.mol

Synonyms:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[(hydroxyphenylacetyl)amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,monosodium salt, [6R-[6a,7b(R*)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-mandelamido-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, monosodiumsalt, D- (8CI);Cefamandole sodium;Cefamandole sodium salt;Kefdole;Sodium7-D-mandelamido-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate;Sodium [6R-[6a,7b(R*)]]-7-[(hydroxyphenylacetyl)amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;

Chemical Property of Sodium cefamandole

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: >175 °C (dec.)
• PSA: 203.97000
• LogP: -1.23150
• Storage Temp.: Store at RT.
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Cefamandole Sodium Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Description: Cefamandole is a cephalosporin antibiotic that is effective against E. coli (MIC values range from 0.25-2 mg/L depending on strain) as well as H. influenza, S. pneumoniae, and S. aureus. It has been used to study the expression and inhibition of penicillin-binding proteins on bacterial cell walls and to study antibiotic resistance.
• Uses: Antibacterial;Bacterial transpeptidase inhibitor Broad-spectrum semi-synthetic cephalosporin antibiotic.

Technology Process of Sodium cefamandole

There total 2 articles about Sodium cefamandole 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:

D-2-phenyl-2-formyloxyacetyl chloride (29169-64-0) + (6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid (24209-38-9) → cefamandole sodium salt (30034-03-8)

Guidance literature:

D-2-phenyl-2-formyloxyacetyl chloride; (6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid; With N,O-bis-(trimethylsilyl)-acetamide; In ethyl acetate; at -10 - 35 ℃; for 1.5h;

With sodium isooctanoate; In ethanol; acetone; at 10 - 32 ℃; for 2h;

Reference yield:

→ cefamandole sodium salt (30034-03-8)

Guidance literature:

Reference yield:

glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) + cefamandole sodium salt (30034-03-8) → N-[(6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyl]-glycine methyl ester (70579-86-1)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1021/jm00192a010

upstream raw materials:

D-2-phenyl-2-formyloxyacetyl chloride

(6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid

Downstream raw materials:

N-[(6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyl]-glycine methyl ester

Refernces

• 1、 -. "Tetrazole derivative". . . Retrieved 2008/06/13.