104146-53-4

Basic information

• Product Name: Cefditoren Acid Sodium Salt
• Synonyms: sodium (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-acetyl]amino]-3-[(E)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetylamino]-3-[(Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid sodium salt;3-[(Z)-2-(4-Methylthiazol-5-yl)vinyl]-7β-[[(Z)-(2-aminothiazol-4-yl)(methoxyimino)acetyl]amino]cepham-3-ene-4-carboxylic acid sodium salt;ME-1206;(6R-(3(Z),6alpha,7beta(Z)))-7-(((2-Amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(2-(4-methyl-5-thiazolyl)ethenyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid monosodium salt;Cefditoren acid sodium salt;Cefditoren sodium;sodium (6R,7R)-7-((Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-((Z)-2-(4-methylthiazol-5-yl)vinyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS NO: 104146-53-4
• Molecular Formula: C₁₉H₁₇N₆O₅S₃*Na
• Molecular Weight: 528.56
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 104146-53-4.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cefditoren Acid Sodium Salt(CAS DataBase Reference)
• NIST Chemistry Reference: Cefditoren Acid Sodium Salt(104146-53-4)
• EPA Substance Registry System: Cefditoren Acid Sodium Salt(104146-53-4)

Safety Data

• Hazardous Substances Data: 104146-53-4(Hazardous Substances Data)

Usage

Uses

Third generation cephalosporin; active metabolite of orally absorbed pivaloyloxymethyl ester prodrug. An antibacterial.

InChI:InChI=1/C19H18N6O5S3.Na/c1-8-11(33-7-21-8)4-3-9-5-31-17-13(16(27)25(17)14(9)18(28)29)23-15(26)12(24-30-2)10-6-32-19(20)22-10;/h3-4,6-7,13,17H,5H2,1-2H3,(H2,20,22)(H,23,26)(H,28,29);/q;+1/b4-3+,24-12+;/t13-,17-;/m1./s1

Upstream product

• 138450-73-4 p-Methoxybenzyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate 
• 64485-88-7 ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate 
• 80756-85-0 (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate 
• 104145-95-1 cefditoren 
• 155723-02-7 (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 
• 104146-14-7 cefditoren acid 
• 84994-24-1 2-methoxyimino-2-(2-aminothiazol-4-yl)acetic acid S-2-benzothiazole ester 
• 64485-89-8 ethyl (Z)-2-(methoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetate 
• 64485-90-1 2-(2-aminothiazol-4-yl)-2-(methoxy)iminoacetic acid 
• 138514-31-5 7-phenylacetamido-3-[(Z)-2-(4-methyl-5-thiazolyl)ethenyl]-4-aminocephalosporanic acid p-methoxybenzylester 
• 119608-99-0 p-Methoxybenzyl 7-amino-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate 
• 119636-62-3 [(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 
• 104146-10-3 (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 
• 82294-70-0 4-methyl-1,3-thiazole-5-carbaldehyde 

Downstream Products

• 117467-28-4 cefditoren pivoxil 

Relevant articles and documents

A spore proper logical sequence of the ester preparation method

The invention belongs to the technical field of medicines and particularly relates to a preparation method of cefditoren pivoxil. The preparation method particularly includes following steps: (1) carrying out a reaction between cefditoren mother nucleus 7ATCA and AE-activated ester with dichloromethane as a solvent under an alkaline condition at 0-5 DEG C; (2) performing extraction with pure water and adding a sodium iso-octoate/acetone solution to obtain cefditoren sodium; (3) carrying out a reaction between the cefditoren sodium and iodomethyl pivalate under the alkaline condition at -40 DEG C to obtain a cefditoren pivoxil solution; (4) adding pure water to separate out a crystal to obtain a crude product of the cefditoren pivoxil. The technical scheme also comprises steps of dissolving the crude product of the cefditoren pivoxil in a mixed solution including dichloromethane and anhydrous ethanol, washing the material solution with a 1% sodium bicarbonate solution and pure water, collecting an organic phase, and performing a pressure-reducing evaporate-drying process to obtain the cefditoren pivoxil being higher than 99% in purity and less in impurities. The preparation method is simple in operation, is easy to control, is high in yield, allows the raw material to be obtained easily and is suitable for industrialized large-scale production.

Preparation method of cefditoren pivoxil

The invention discloses a preparation method of an important antibiotic cefditoren pivoxil. The preparation method comprises that 7-ATCA as a raw material is bonded to an AE active ester under base catalysis so that cefditoren acid is obtained, the cefditoren acid and sodium bicarbonate undergo a reaction to produce a salt, and the salt and cefditoren pivoxil undergo a replacement reaction under alkaline conditions to produce 2, 2-dimethylpropionyloxy(6R, 7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-[(Z)-2-(4-methyl-1, 3-thiazolyl-5-yl)vinyl]-8-oxo-5-thia-1-azabicyalo[4. 2. 0]octyl-2-ene-2-formate. The preparation method has the advantages of low cost, simple operation, high purity, use of cheap and easily available raw materials, industrial production feasibility and small pollution.

DEPLETION OF E-ISOMERS IN PREPARATION OF Z-ENRICHED 3-(2-SUBSTITUTED VINYL) CEPHALOSPORINS

The present invention relates to depleting E-isomers of 3-(2-substituted vinyl) cephalosporins from a Z/E mixture of the same by selective crystallization techniques. The present invention to Z-enriched compounds comprising less than 5 % E-isomer.