TopiraMate N-Methyl IMpurity

Base Information

• Chemical Name: TopiraMate N-Methyl IMpurity
• CAS No.: 97240-80-7
• Molecular Formula: C13H23NO8S
• Molecular Weight: 353.39
• Mol file: 97240-80-7.mol

Synonyms:TopiraMate N-Methyl IMpurity;N-Methyl TopiraMate

Chemical Property of TopiraMate N-Methyl IMpurity

Chemical Property:

• Boiling Point: 424.9±55.0 °C (760 mmHg)
• PSA: 109.93000
• Density: 1.282±0.06 g/cm3(20 °C , 760mmHg)
• LogP: 1.33700
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

95% ^*data from raw suppliers

Topiramate N-methyl impurity ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Methyl Topiramate, is an impurity of Topiramate (T540250); which is an anticonvulsant (antiepilepsy) drug, that has been approved for weight loss by FDA.

Technology Process of TopiraMate N-Methyl IMpurity

There total 5 articles about TopiraMate N-Methyl IMpurity 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: 98.0%

2,3;4,5-di-O-isopropylidene-β-D-fructopyranose (20880-92-6) + N-methylsulfamoyl chloride (10438-96-7) → 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose methylsulfamate (97240-80-7)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 2h; Inert atmosphere;

DOI:10.1039/d1ob00326g

Reference yield: 86.0%

topiramate (97240-79-4) + methyl iodide (74-88-4) → 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose methylsulfamate (97240-80-7)

Guidance literature:

With potassium fluoride on basic alumina; In acetonitrile; at 80 ℃; for 48h;

DOI:10.1080/17415993.2015.1069294

Reference yield:

2,3;4,5-di-O-isopropylidene-β-D-fructopyranose (20880-92-6) + methylamine (74-89-5) → 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose methylsulfamate (97240-80-7)

Guidance literature:

With pyridine; sulfuryl dichloride; Yield given. Multistep reaction; 1.) CH₂Cl₂, RT, 2 h, 2.) acetonitrile, 3 d;

DOI:10.1021/jm00388a023

upstream raw materials:

2,3;4,5-di-O-isopropylidene-β-D-fructopyranose

N-methylsulfamoyl chloride

methylamine

topiramate

Refernces

• 1、 Saeidian, Hamid,Abdoli, Morteza. "The first general protocol for N-monoalkylation of sulfamate esters: Benign synthesis of N-alkyl Topiramate (anticonvulsant drug) derivatives". . p. 463 - 470. Retrieved 2015/10/19.