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
• Article Data: 7

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 
• 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 
• 138514-31-5 7-phenylacetamido-3-[(Z)-2-(4-methyl-5-thiazolyl)ethenyl]-4-aminocephalosporanic acid p-methoxybenzylester 

Downstream Products

• 104145-95-1 cefditoren 
• 117467-28-4 cefditoren pivoxil 
• 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 
• 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 

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.

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.

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.