CID 13591236

Base Information

• Chemical Name: CID 13591236
• CAS No.: 103121-85-3
• Molecular Formula: C13H20N3O3S.Cl
• Molecular Weight: 333.83400
• Hs Code.: 2941906000
• Mol file: 103121-85-3.mol

Synonyms:SCHEMBL9602368;UVKYDOZUOXJZSR-WYUVZMMLSA-N;J-000878

Chemical Property of CID 13591236

Chemical Property:

• Vapor Pressure: 0Pa at 25℃
• Boiling Point: 681℃[at 101 325 Pa]
• PSA: 111.76000
• Density: 1.61[at 20℃]
• LogP: -0.12780
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly), Water (Slightly)
• Water Solubility.: 111g/L at 20℃
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 333.0913904
• Heavy Atom Count: 21
• Complexity: 494

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-[[(6R,7R)-7-Amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methylpyrrolidiniumChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+]1(CCCC1)CC2=C(N3C(C(C3=O)N)SC2)C(=O)[O-].Cl
• Isomeric SMILES: C[N+]1(CCCC1)CC2=C(N3[C@@H]([C@@H](C3=O)N)SC2)C(=O)[O-].Cl
• Uses: 1-[[(6R,7R)-7-Amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methylpyrrolidinium Chloride is an impurity in the synthesis of Cefepime (C242750), a semisynthetic, fourth generation cephalosporin antibiotic. Antibacterial.

Technology Process of CID 13591236

There total 6 articles about CID 13591236 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: 86.5%

C21H26N3O4S(1+)*Cl(1-) → 1-[((6R,7R)-7-amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]-1-methylpyrrolidinium chloride (103121-85-3)

Guidance literature:

With ammonium hydroxide; In water; at 27 ℃; for 0.166667h; pH=8; Temperature; pH-value; Enzymatic reaction;

Reference yield:

7-amino-3-[(1-methyl-1-pyrrolidinium)methyl]ceph-3-em-4-carboxylate → 1-[(7-amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]-1-methyl-pyrrolidinium-chloride (103121-85-3)

Guidance literature:

With hydrogenchloride; triethylamine; In dichloromethane; water; acetone; at -20 - 25 ℃; for 1.25h; pH=2.5;

Reference yield:

(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (104146-10-3) → 1-[((6R,7R)-7-amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]-1-methylpyrrolidinium chloride (103121-85-3)

Guidance literature:

Multi-step reaction with 3 steps

1: formic acid / chloroform / 16 h / -30 °C

2: ethyl acetate / 2 h / -30 °C

3: ammonium hydroxide / water / 0.17 h / 27 °C / pH 8 / Enzymatic reaction

With ammonium hydroxide; formic acid; In chloroform; water; ethyl acetate;

upstream raw materials:

1-Methylpyrrolidine

3-acetoxy-7-trimethylsilylamino-3-cephem-4-carboxylic acid trimethylsilyl ester

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

(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Downstream raw materials:

1-[[(6R,7R)-7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methyl-pyrrolidinium chloride hydrochloride

cefepime sulfate

Refernces

• 1、 -. "PROCESS FOR PRODUCTION OF INTERMEDIATES FOR USE IN CEFALOSPORIN SYNTHESIS". Page/Page column 9; 12-15. . Retrieved 2008/06/13.