Cefmenoxime

Base Information

• Chemical Name: Cefmenoxime
• CAS No.: 65085-01-0
• Molecular Formula: C₁₆H₁₇N₉O₅S₃
• Molecular Weight: 511.566
• UNII: KBZ4844CXN
• DSSTox Substance ID: DTXSID2022755
• Wikipedia: Cefmenoxime
• NCI Thesaurus Code: C65295
• Metabolomics Workbench ID: 42662
• ChEMBL ID: CHEMBL1201224
• Mol file: 65085-01-0.mol

Synonyms:Abbott 50192;Abbott-50192;Abbott50192;Cefmax;Cefmenoxime;Cefmenoxime Hydrochloride;Cefmenoxime Hydrochloride (2:1);Hydrochloride, Cefmenoxime;SCE 1365;SCE-1365;SCE1365

Chemical Property of Cefmenoxime

Chemical Property:

• Appearance/Colour: White or light yellow crystalline powder, odourless
• PKA: 2.61±0.50(Predicted)
• PSA: 269.65000
• Density: 1.96 g/cm³
• LogP: 0.04020
• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 8
• Exact Mass: 511.05147820
• Heavy Atom Count: 33
• Complexity: 890

Purity/Quality:

97% ^*data from raw suppliers

Cefmenoxime ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)O
• Isomeric SMILES: CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)O
• Uses: Cefmenoxime (cas# 65085-01-0) is a compound useful in organic synthesis. Antibacterial.
• Therapeutic Function: Antibacterial

Technology Process of Cefmenoxime

There total 7 articles about Cefmenoxime 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: 73.0%

(6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid (24209-38-9) + (2-Amino-thiazol-4-yl)-[(Z)-methoxyimino]-acetic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester (207725-19-7) → cefmenoxime (65085-01-0)

Guidance literature:

With N,O-bis-dimethylsilyl acetamide; at 0 ℃; for 2.5h;

DOI:10.1080/00397919808006831

Reference yield: 70.3%

3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24209-38-9) + 4-(diethylphosphoryl)-2-(2-amino-4-thiazolyl)-2-syn-(2-methoxyimino)acetate (179258-53-8) → (6R)-7t-[2-(2-amino-thiazol-4-yl)-2-(Z)-methoxyimino-acetylamino]-8-oxo-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (65085-01-0,66340-45-2,69738-54-1)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 2.5h;

DOI:10.1080/00397919808005071

Reference yield:

cefotaxime (65872-41-5) → (6R)-7t-[2-(2-amino-thiazol-4-yl)-2-(Z)-methoxyimino-acetylamino]-8-oxo-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (65085-01-0,66340-45-2,69738-54-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / N,N-diisopropylethylamine / dimethylformamide / 2 h / 0 - 5 °C

2: 70.3 percent / Et₃N / dimethylformamide / 2.5 h

With triethylamine; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1080/00397919808005071

upstream raw materials:

3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

4-(diethylphosphoryl)-2-(2-amino-4-thiazolyl)-2-syn-(2-methoxyimino)acetate

cefotaxime

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