155723-02-7

Basic information

• Product Name: (6R,7R)
• Synonyms: (6R,7R);(6R,7R)-7-Amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R,7R)-7-AMino-3-[(Z)-2-(4-Methylthiazol-5-yl)ethenyl]-3-cepheM-4-carboxylic Acid;7-AMTCA;7-ATCA;Parent nucleus of Cefditoren(7-AMTCA);Parent nucleus of Cefditoren;(6R,2R)-7-aMino-3- (1z)-2-(4-M...
• CAS NO: 155723-02-7
• Molecular Formula: C₁₃H₁₃N₃O₃S₂
• Molecular Weight: 323.39062
• EINECS: 1308068-626-2
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Nucleus of cefditoren
• Mol File: 155723-02-7.mol

Chemical Properties

• Boiling Point: 642.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.59
• Solubility: DMSO, Water
• PKA: 2.36±0.50(Predicted)
• CAS DataBase Reference: (6R,7R)(CAS DataBase Reference)
• NIST Chemistry Reference: (6R,7R)(155723-02-7)
• EPA Substance Registry System: (6R,7R)(155723-02-7)

Safety Data

• Hazardous Substances Data: 155723-02-7(Hazardous Substances Data)

Upstream product

• 82294-70-0 4-methyl-1,3-thiazole-5-carbaldehyde 
• 57268-16-3 5-bromo-2-methyl-1,3-thiazole 
• 957-68-6 7-Aminocephalosporanic acid 
• 15690-38-7 (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 138514-31-5 7-phenylacetamido-3-[(Z)-2-(4-methyl-5-thiazolyl)ethenyl]-4-aminocephalosporanic acid p-methoxybenzylester 
• 1385032-85-8 7-amino-3-[(Z)-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid dicyclohexylamine salt 
• 166581-61-9 7-amino-3-[(E)-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid dicyclohexylamine salt 
• 1207515-78-3 C₁₃H₁₂N₃O₃S₂^(1-)*Na⁽¹⁺⁾ 
• 823792-22-9 7-phenylacetamido-3-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid 

Downstream Products

• 104145-95-1 cefditoren 
• 117467-28-4 cefditoren pivoxil 
• 1385032-85-8 7-amino-3-[(Z)-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid dicyclohexylamine salt 
• 166581-61-9 7-amino-3-[(E)-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid dicyclohexylamine salt 
• 148774-47-4 (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-[(Z)-2-(4-methylthiazol-5-yl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid 2,2-dimethylpropionyloxymethyl ester 
• 104146-53-4 7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt 

Relevant articles and documents

Preparation method of cefdiaxone pivoxil

The invention relates to a preparation method of Cefditoren Pivoxil. The preparation method comprises steps as follows: 7-ACA (3-acetyloxymethyl-5-thio-7-amino-8-oxy-1-nitrogen heterobicyclic octyl-2-ene-2 carboxylic acid) is taken as a starting raw material and is subjected to iodination and Wittig reaction after silanization protection, and a Cefditoren parent nucleus 7-ATCA (7-amino-3-[(Z)-2-(4-methyl-5-thiazole) vinyl]-3-cephem-4-carboxylic acid) is generated; after amino protection of aminothiazole ethyl gallate, a compound 2 is produced from 7-ATCA under catalysis of AlMe3; the compound2 is subjected to an esterification reaction with iodomethyl pivalate under actions of a phase transfer catalyst and an acid adsorbent, the amino protection is removed, and a target product CefditorenPivoxil is obtained. According to the preparation method, reaction conditions are mild, product purity and yield are high, the process is stable, amplification is easy, and the method is applicable to industrial production.

Preparation method of cefditoren pivoxil

The invention relates to a preparation method of cefditoren pivoxil. The preparation method comprises the following steps: 7-aminocephalosporanic acid(ACA) is taken as a starting material and subjected to a series of reactions such as iodination and the like after silylation protection to generate parent nucleus for cefditoren, namely 7-amino-3-[(Z)-2-(4-methyl-5-thiazolyl)ethenyl]-3-cephem-4-carboxylic acid (7-ATCA); the compound 7-ATCA firstly reacts with sodium iso-octoate to form sodium salt and then reacts with ethyl 2-(2-aminothiazole-4-yl)-2-methoxyiminoacetate to generate a compound 2,namely cefditoren sodium, under the catalysis of immobilized penicillin acylase; and then the cefditoren sodium reacts with iodomethyl pivalate to obtain a target product, namely cefditoren pivoxil.The preparation method is mild in reaction conditions, environmentally-friendly, high in conversion rate, simple in process, high in content of cis isomers, easy to enlarge and suitable for industrialproduction.

Method for synthesizing cefditoren pivoxil

The invention relates to a method for synthesizing cefditoren pivoxil. The method comprises that D-7ACA reacts with an oxidizing reagent to produce a compound 1, the compound 1 is protected through silanization to produce a compound 2, 4-methylthiazole-5-methanol and NaI undergo an iodination reaction in the presence of a small amount of sulfuric acid for catalysis, triphenylphosphine is added into the reaction system and undergoes a reaction to produce a compound 3, the compound 3 is added into the compound 2 liquid and undergoes a reaction, the reaction product is concentrated, methanol anda small amount of concentrated hydrochloric acid are added into the concentrated product, the concentrated product is deprotected and crystallized to form cefditoren mother nucleuses, 7-ATCA and an AEactive ester undergo a reaction under alkaline conditions, the reaction product is crystallized to form a cefditoren sodium wet product, the cefditoren sodium wet product is added into iodomethyl pivalate and undergoes a reaction in the presence of a phase transfer catalyst and the product is crystallized to form a cefditoren pivoxil crude product. In preparation of the compound 1, cefditoren sodium and cefditoren pivoxil, single solvents are used and are easy to recover. The method has the advantages of simple operation, high product conversion rate, few impurities and low production cost and is suitable for industrial production of cefditoren pivoxil.

A process for the preparation of intermediates esterspore proper logical sequence

The invention discloses a synthesis method of a drug intermediate, and particularly relates to a preparation method of a cefditoren pivoxil cephalosporins intermediate. The preparation method comprises the step of reacting through phosphorus Ylide-Wittig reaction and hydrolysis reaction by using 7-phenylacetamide-3-chloromethylcephalosporanic acid p-methoxybenzyl ester to obtain cefditoren pivoxil cephalosporins. The preparation method is simple in process, safe, environment-friendly, high in yield, and suitable for industrialized production.

3-ALKENYLCEPHEM COMPOUNDS AND PROCESS FOR PRODUCTION THEREOF

A 3-alkenylcephem compound of the formula (1) wherein R 1 is benzyl or phenoxymethyl, R 2 , R 3 and R 4 are alike or different and are each a hydrogen atom, C 1-10 alkyl, C 4-8 cycloalkyl or aryl C 1-3 alkyl substituted or unsubstituted with C 1-4 alkyl, R 2 and R 3 , when taken together, form a group -(CH 2 ) 1 X m (CH 2 ) n - substituted or unsubstituted with C 1-4 alkyl at an optional position, X is an oxygen atom or group -N(R 5 )-, 1 is 0 to 3, m is 0 or 1, n is an integer of 2 to 4, R 5 is a hydrogen atom or C 1-4 alkyl.

PROCESS FOR PRODUCTION OF 3-ALKENYLCEPHEM COMPOUNDS

A process for preparing 7-amino-3-[(E/Z)-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid of the formula (1) and an alkali metal salt thereof, said acid and said salt being improved in the content of 7-amino-3-[(Z)-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid of the formula (2) or an alkali metal salt thereof, the process being characterized in that an aqueous solution of an alkali metal salt of 7-amino-3-[(E/Z)-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid of the formula (1) is treated with a high porous polymer and/or active carbon as added thereto.

AN IMPROVED PROCESS FOR THE PREPARATION OF CEFDITOREN

The present invention relates to an improved process for the preparation of Cefditoren of formula (I), the said process comprising the steps of: i) converting the compound of formula (II) to a compound of the formula (III) using TPP and sodium iodide in the presence of THF, water, and base; ii) reacting the compound of formula (III) with 4-methyl-5-formyl-thiazole to produce a compound of formula (IV); iii) deesterifying the compound of the formula (IV) to yield compound of formula (V); iv) converting the compound of formula (V) to compound of formula (VI) in the presence of a base and solvent; v) converting the compound of formula (VI) into compound of formula (VII) by enzymatic hydrolysis; and vi) reacting compound of formula (VII) with compound of formula (VIII) in the presence of solvent and base to produce compound of formula (I).