Cefcapene

Base Information

• Chemical Name: Cefcapene
• CAS No.: 135889-00-8
• Molecular Formula: C₁₇H₁₉N₅O₆S₂
• Molecular Weight: 453.5
• Hs Code.: 2942000000
• UNII: 4D5D3422MW
• DSSTox Substance ID: DTXSID201027544
• Nikkaji Number: J402.887B
• Wikipedia: Cefcapene
• Wikidata: Q5057225
• NCI Thesaurus Code: C76160
• Metabolomics Workbench ID: 154267
• ChEMBL ID: CHEMBL582912
• Mol file: 135889-00-8.mol

Synonyms:S 1006;S-1006

Chemical Property of Cefcapene

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 936°Cat760mmHg
• Flash Point: 519.9°C
• PSA: 231.48000
• Density: 1.63
• LogP: 1.96290
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 453.07767569
• Heavy Atom Count: 30
• Complexity: 832

Purity/Quality:

98%Min ^*data from raw suppliers

Cefcapene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O
• Isomeric SMILES: CC/C=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O
• Uses: Cefcapene is a metabolite of Cefcapene Pivoxil (C242550). Antibacterial, orally absorbed cephalosporin.

Technology Process of Cefcapene

There total 3 articles about Cefcapene 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: 87.2%

diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylate (105890-09-3) → cefcapene (135889-00-8)

Guidance literature:

With aluminium trichloride; In dichloromethane; at -30 ℃; for 0.5h;

DOI:10.7164/antibiotics.47.466

Reference yield:

(6R,7R)-7-Amino-3-carbamoyloxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester; compound with toluene-4-sulfonic acid → cefcapene (135889-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) triethylamine, methanesulfonyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -50 deg C, 2.) CH₂Cl₂, -50 deg C

2: 87.2 percent / AlCl₃ / CH₂Cl₂; various solvent(s) / 0.5 h / -30 °C

With aluminium trichloride; methanesulfonyl chloride; triethylamine; In dichloromethane;

DOI:10.7164/antibiotics.47.466

Reference yield:

(Z)-2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]pent-2-enoic acid (86978-24-7) → cefcapene (135889-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) triethylamine, methanesulfonyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -50 deg C, 2.) CH₂Cl₂, -50 deg C

2: 87.2 percent / AlCl₃ / CH₂Cl₂; various solvent(s) / 0.5 h / -30 °C

With aluminium trichloride; methanesulfonyl chloride; triethylamine; In dichloromethane;

DOI:10.7164/antibiotics.47.466

upstream raw materials:

diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylate

(Z)-2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]pent-2-enoic acid

Refernces