Cefotaxime Proxetil

Base Information

• Chemical Name: Cefotaxime Proxetil
• CAS No.: 217803-89-9
• Molecular Formula: C₂₂H₂₇N₅O₁₀S₂
• Molecular Weight: 585.616
• UNII: CRY6JYK2W6
• Mol file: 217803-89-9.mol

Synonyms:Cefotaxime Proxetil;217803-89-9;CRY6JYK2W6;1-propan-2-yloxycarbonyloxyethyl (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;(1RS)-1-(((1-Methylethoxy)carbonyl)oxy)ethyl (6R,7R)-3-(acetoxymethyl)-7-(((2Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate;5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-7-(((2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl)amino)-8-oxo-, 1-(((1-methylethoxy)carbonyl)oxy)ethyl ester, (6R,7R)-;UNII-CRY6JYK2W6;Cefpodoxime proxetil impurity E [EP];CEFPODOXIME PROXETIL IMPURITY E [EP IMPURITY]

Chemical Property of Cefotaxime Proxetil

Chemical Property:

• Melting Point: 107 - 113°C
• PKA: 8.11±0.60(Predicted)
• Density: 1.60±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 14
• Exact Mass: 585.11993442
• Heavy Atom Count: 39
• Complexity: 1070

Purity/Quality:

90% ^*data from raw suppliers

CefotaximeProxetil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)OC(=O)OC(C)OC(=O)C1=C(CSC2N1C(=O)C2NC(=O)C(=NOC)C3=CSC(=N3)N)COC(=O)C
• Isomeric SMILES: CC(C)OC(=O)OC(C)OC(=O)C1=C(CS[C@H]2N1C(=O)[C@H]2NC(=O)/C(=N\OC)/C3=CSC(=N3)N)COC(=O)C
• Uses: Cefotaxime Proxetil (Cefpodoxime Proxetil EP Impurity E) is an impurity of Cefotaxime (C242950), which is a broad spectrum third generation cephalosporin antibiotic. The name Cefotaxime applies to the isomer having a syn-methoxy imino group.

Technology Process of Cefotaxime Proxetil

There total 2 articles about Cefotaxime Proxetil 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: 82.0%

1-(isopropoxycarbonyloxy)ethyl chloride (98298-66-9) + cefotaxime sodium salt (60846-23-3) → 1-(isopropoxycarbonyloxy)ethyl 7β-<2-(2-aminothiazol-4-yl)-(Z)-methoxyiminoacetamido>-3-acetoxymethyl-3-cephem-4-carboxylate (217803-89-9)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; In N,N-dimethyl-formamide; at 40 - 45 ℃; for 18h;

DOI:10.1080/00397919808004469

Reference yield: 75.0%

1-iodoethyl isopropyl carbonate (84089-73-6,91508-00-8) + (6R)-3-acetoxymethyl-7t-[2-(2-amino-thiazol-4-yl)-2-(Z)-methoxyimino-acetylamino]-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (60846-21-1,63527-52-6,63527-53-7,152186-43-1) → 1-(isopropoxycarbonyloxy)ethyl 7β-<2-(2-aminothiazol-4-yl)-(Z)-methoxyiminoacetamido>-3-acetoxymethyl-3-cephem-4-carboxylate (217803-89-9)

Guidance literature:

With potassium carbonate; caesium carbonate; In 1,4-dioxane; N,N-dimethyl-formamide; at 5 ℃; for 1.5h;

DOI:10.1080/00397919908086176

upstream raw materials:

1-(isopropoxycarbonyloxy)ethyl chloride

cefotaxime sodium salt

1-iodoethyl isopropyl carbonate

(6R)-3-acetoxymethyl-7t-[2-(2-amino-thiazol-4-yl)-2-(Z)-methoxyimino-acetylamino]-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Refernces

• 1、 Lee, Hong Woo,Kang, Tae Won,Kim, Eung-Nam,Shin, Jaewook,Cha, Kyung Hoi,Cho, Dong Ock,Choi, Nam Hee,Kim, Jung-Woo,Hong, Chung Il. "An effective and convenient esterification of cephalosporin derivatives by using quarternary ammonium salts as catalysts". . p. 4345 - 4354. Retrieved 1998.