Cefditoren sodium

Base Information

• Chemical Name: Cefditoren sodium
• CAS No.: 104146-53-4
• Molecular Formula: C19H17N6NaO5S3
• Molecular Weight: 528.569
• Mol file: 104146-53-4.mol

Synonyms:cefditoren;cefditoren, sodium salt, (6R-(3(Z),6alpha,7beta(Z)))-isomer;ME 1206;ME-1206

Chemical Property of Cefditoren sodium

Chemical Property:

• PSA: 244.71000
• LogP: 0.86800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 529.03985050
• Heavy Atom Count: 34
• Complexity: 928

Purity/Quality:

99% ^*data from raw suppliers

Cefditoren acid sodium salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(SC=N1)C=CC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)O.[Na+]
• Isomeric SMILES: CC1=C(SC=N1)/C=C/C2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N/OC)/C4=CSC(=N4)N)SC2)C(=O)O.[Na+]
• Uses: Third generation cephalosporin; active metabolite of orally absorbed pivaloyloxymethyl ester prodrug. An antibacterial.

Technology Process of Cefditoren sodium

There total 19 articles about Cefditoren sodium 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: 90.0%

cefditoren (104145-95-1) → 7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt (104146-53-4)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at 30 - 35 ℃; for 4h;

Reference yield: 83.9%

(6R,7R)-7-amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (155723-02-7) + (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) → 7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt (104146-53-4)

Guidance literature:

(6R,7R)-7-amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; With sulphurous acid; triethylamine; In methanol; dichloromethane; at 0 - 5 ℃; for 4h; Darkness;

With (+/-)-2-n-ethylpentanoic acid sodium salt; In water; acetone; at 20 - 25 ℃; for 2h; Temperature;

Reference yield: 75.0%

7-amino-3-[2-(4-methyl-5-thiazolyl)vinyl]-3-cephem-4-carboxylic acid + (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) → 7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt (104146-53-4)

Guidance literature:

7-amino-3-[2-(4-methyl-5-thiazolyl)vinyl]-3-cephem-4-carboxylic acid; (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; With triethylamine; In tetrahydrofuran; water; at 0 - 5 ℃; for 2.25 - 3.33333h;

With sodium 2-ethylhexanoic acid; In tetrahydrofuran; water; acetone; at 20 - 25 ℃;

upstream raw materials:

p-Methoxybenzyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate

4-methyl-1,3-thiazole-5-carbaldehyde

(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

[(6R,7R)-2-(4-Methoxy-benzyloxycarbonyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl]-triphenyl-phosphonium; iodide

Downstream raw materials:

cefditoren pivoxil

Refernces

• 1、 -. "Preparation method of cefditoren pivoxil". . . Retrieved 2017/02/24.
• 2、 -. "DEPLETION OF ISOMER IN CEPHALOSPORIN ANTIBIOTIC". Page/Page column 5. . Retrieved 2008/06/13.