Cefpodoxime Proxetil,(S)

Base Information

• Chemical Name: Cefpodoxime Proxetil,(S)
• CAS No.: 80210-62-4
• Molecular Formula: C15H17N5O6S2
• Molecular Weight: 427.462
• European Community (EC) Number: 685-334-0
• Wikipedia: Cefpodoxime
• NCI Thesaurus Code: C65305
• RXCUI: 20489
• Mol file: 80210-62-4.mol

Synonyms:cefpodoxime;R 3746;R 3763;R-3746;R-3763;RU 51746;RU-51746;U 76253A;U-76,253A

Chemical Property of Cefpodoxime Proxetil,(S)

Chemical Property:

• Appearance/Colour: off-white solid
• Melting Point: 200-202 °C
• Refractive Index: 1.78
• PKA: 2.77±0.50(Predicted)
• PSA: 209.98000
• Density: 1.785 g/cm³
• LogP: 0.37080
• Storage Temp.: -20°C Freezer
• Sensitive.: Light Sensitive
• Solubility.: Soluble in DMSO
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 427.06202563
• Heavy Atom Count: 28
• Complexity: 744

Purity/Quality:

99% ^*data from raw suppliers

CefpodoximeAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 22-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCC1=C(N2C(C(C2=O)NC(=O)C(=NOC)C3=CSC(=N3)N)SC1)C(=O)O
• Isomeric SMILES: COCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)C(=NOC)C3=CSC(=N3)N)SC1)C(=O)O
• Uses: A metabolite of Cefpodoxime Proxetil. An antibacterial. A metabolite of Cefpodoxime Proxetil (C243860). An antibacterial. Cefpodoxime Proxetil metabolite antibiotic
• Clinical Use: Cefpodoxime has been used principally for the treatment of upper and lower respiratory tract infections in children and adults.

Technology Process of Cefpodoxime Proxetil,(S)

There total 11 articles about Cefpodoxime Proxetil,(S) 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: 82.86%

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → cefpodoxime (80210-62-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; at -5 - 5 ℃; for 2h;

Reference yield: 82.2%

sodium methylate (124-41-4) + (Z)-α-(methoxyimino)-2-amino-4-thiazoleacetyl chloride (75994-59-1) + 7-amino-3-chloromethyl-3-cephem-4-carboxylic acid → cefpodoxime (80210-62-4)

Guidance literature:

sodium methylate; 7-amino-3-chloromethyl-3-cephem-4-carboxylic acid; With benzyltrihexylammonium chloride; potassium iodide; In dimethyl sulfoxide; at 15 ℃; for 8h;

(Z)-α-(methoxyimino)-2-amino-4-thiazoleacetyl chloride; In dimethyl sulfoxide; at 10 ℃; for 4h; Temperature; Solvent; Reagent/catalyst;

Reference yield:

(benzothiazol-2-yl)-2-(2-aminothiazol-4-yl)-Z-2-methoxyimino-thioacetate (959246-33-4) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → cefpodoxime (80210-62-4)

Guidance literature:

(benzothiazol-2-yl)-2-(2-aminothiazol-4-yl)-Z-2-methoxyimino-thioacetate; (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; With triethylamine; In methanol; water; at 15 - 20 ℃;

With sulfuric acid; In methanol; water;

upstream raw materials:

(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate

(6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

7-Aminocephalosporanic acid

Downstream raw materials:

cefpodoxime proxetil

1-(isopropoxycabonyloxy) ethyl (6R, 7R) [7-[2-(2-AMINOTHIAZOL-4-YL)-2-METHOXYIMINO-] [ACETAMIDO]-3-(METHOXYMETHYL) 3-CEPHEM-4-CARBOXYLATE]

1-(ethoxycarbonyloxy)ethyl (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-3-cephem-4-carboxylate

(R)-1-(isopropoxycarbonyloxy)ethyl-(+)-(6R,7R)-7-[2-(2-amino-4-thiazolyl)-2-((Z)-methoxyimino)acetamido]-3-methoxymethyl-8-oxo-5-thia-1-azabicyclo[4,2,0]oct-2-en-2-carboxylate

Refernces

• 1、 Pieper, Matthias,Schleich, Herbert,Gr?ger, Harald. "General Synthesis of Industrial Cephalosporin-Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent". . p. 3259 - 3263. Retrieved 2019/06/04.
• 2、 -. "Synthesis method of cefpodoxime proxetil intermediate". Paragraph 0010; 0011; 0012. . Retrieved 2016/11/09.