N-(7-Aminocephem-3-em-3-ylmethyl)pyridinium-4-carboxylate hydriodide

Base Information

• Chemical Name: N-(7-Aminocephem-3-em-3-ylmethyl)pyridinium-4-carboxylate hydriodide
• CAS No.: 100988-63-4
• Molecular Formula: C₁₃H₁₄N₃O₃S*I
• Molecular Weight: 419.243
• European Community (EC) Number: 423-260-0
• UNII: G9113PML9Z
• Wikidata: Q27278955
• Mol file: 100988-63-4.mol

Synonyms:100988-63-4;Pyridinium, 1-(((6R,7R)-7-amino-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-, iodide (1:1);Pyridinium, 1-[[(6R,7R)-7-amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, iodide (1:1);N-(7-Aminocephem-3-em-3-ylmethyl)pyridinium-4-carboxylate hydriodide;Q27278955;PYRIDINIUM, 1-(((6R,7R)-7-AMINO-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-, IODIDE;PYRIDINIUM, 1-((7-AMINO-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-, IODIDE, (6R-TRANS)-

Chemical Property of N-(7-Aminocephem-3-em-3-ylmethyl)pyridinium-4-carboxylate hydriodide

Chemical Property:

• PSA: 112.81000
• LogP: -2.80260
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 418.98006
• Heavy Atom Count: 21
• Complexity: 474

Purity/Quality:

99.9% ^*data from raw suppliers

7-Amino-3-(1-pyridylmethyl)-3-cephem-4-carboxylicAcidHydroiodide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=C(N2C(S1)C(C2=O)N)C(=O)O)C[N+]3=CC=CC=C3.[I-]
• Isomeric SMILES: C1C(=C(N2[C@H](S1)[C@@H](C2=O)N)C(=O)O)C[N+]3=CC=CC=C3.[I-]
• Uses: 7-Amino-3-(1-pyridylmethyl)-3-cephem-4-carboxylic acid Hydroiodide, is an impurity of Ceftazidime (C244100). Ceftazidime impurity B.

Technology Process of N-(7-Aminocephem-3-em-3-ylmethyl)pyridinium-4-carboxylate hydriodide

There total 5 articles about N-(7-Aminocephem-3-em-3-ylmethyl)pyridinium-4-carboxylate hydriodide 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)-Trimethylsilyl 7-[((Trimethylsilyl)oxy)carbonyl]-amino-3-acetoxymethylceph-3-em-4-carboxylate (111390-00-2) → 3-<(1-pyridinio)methyl>cephem (100988-63-4,106937-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1: iodotrimethylsilane / CH₂Cl₂ / 1 h

2: 2.) MeOH / 1.) CH₂Cl₂, 90 min, 2.) from 0 to 5 deg C, 15 min

With methanol; trimethylsilyl iodide; In dichloromethane;

DOI:10.1021/jo00240a009

Reference yield:

(6R,7R)-Trimethylsilyl 7-(Trimethylsilyl)amino-3-acetoxy methylceph-3-em-4-carboxylate (31461-04-8) → 3-<(1-pyridinio)methyl>cephem (100988-63-4,106937-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1: iodotrimethylsilane (TMSI) / 1,1,2-trichloro-1,2,2-trifluoro-ethane / 2 h / 25 - 30 °C

2: 2.) MeOH / 1.) CH₂Cl₂, from 0 to 5 deg C, 3.5 h, 2.) from 0 to 5 deg C, 10 min

With methanol; trimethylsilyl iodide; In 1,1,2-Trichloro-1,2,2-trifluoroethane;

DOI:10.1021/jo00240a009

Reference yield:

pyridine (110-86-1) + (6R,7R)-trimethylsilyl 7-(trimethylsilyl)amino-3-iodomethylceph-3-em-4-carboxylate (106134-67-2) → 3-<(1-pyridinio)methyl>cephem (100988-63-4,106937-15-9)

Guidance literature:

With methanol; Yield given. Multistep reaction; 1.) CH₂Cl₂, from 0 to 5 deg C, 3.5 h, 2.) from 0 to 5 deg C, 10 min;

DOI:10.1021/jo00240a009

upstream raw materials:

pyridine

(6R,7R)-trimethylsilyl 7-(trimethylsilyl)amino-3-iodomethylceph-3-em-4-carboxylate

(6R,7R)-Trimethylsilyl 7-[((Trimethylsilyl)oxy)carbonyl]-amino-3-iodomethylceph-3-em-4-carboxylate

(6R,7R)-Trimethylsilyl 7-(Trimethylsilyl)amino-3-acetoxy methylceph-3-em-4-carboxylate

Downstream raw materials:

(Z)-7-(2-(2-aminothiazol-4-yl)-2-(((1-(tertbutoxy)-2-methyl-1-oxopropan-2-yl)oxy)amino)acetamido)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylate