178601-88-2

Basic information

• Product Name: (Z)-Cefdinir
• Synonyms: (6R,7R)-7-[[(2E)-(2-AMino-4-thiazolyl)(hydroxyiMino)acetyl]aMino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;(E)-Cefdinir;(Z)-Cefdinir
• CAS NO: 178601-88-2
• Molecular Formula: C14H13N5O5S2
• Molecular Weight: 395.41352
• Product Categories: Pharmaceuticals;Sulfur & Selenium Compounds;Chiral Reagents;Impurity;Intermediates & Fine Chemicals
• Mol File: 178601-88-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility: Dichloromethane (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (Z)-Cefdinir(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-Cefdinir(178601-88-2)
• EPA Substance Registry System: (Z)-Cefdinir(178601-88-2)

Safety Data

• Hazardous Substances Data: 178601-88-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-Cefdinir is used as an impurity in Cefdinir (C242670) for quality control and assurance purposes. It helps in the development and manufacturing process of Cefdinir to ensure the purity and effectiveness of the final antibiotic product. By monitoring and controlling the presence of (Z)-Cefdinir, pharmaceutical companies can maintain the safety and efficacy of Cefdinir as a treatment for bacterial infections.

Upstream product

• 128454-32-0 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid 
• 79349-82-9 (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 91832-41-6 potassium syn-7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate 
• 64276-70-6 (6R,7R)-3-Bromomethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 64485-82-1 (Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate 
• 28240-15-5 3-hydroxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic 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 
• 69689-86-7 ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino)acetate 
• 94796-13-1 diphenylmethyl 7β-phenylacetamido-3-vinyl-3-cephem-4-carboxylate 
• 35246-64-1 (6R,7R)-benzhydryl 3-(hydroxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 110130-88-6 (Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetic acid 
• 104797-47-9 S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate 
• 127770-93-8 C₁₆H₁₅N₅O₆S₂ 

Downstream Products

• 946573-41-7 cefdinir lactone 
• 178422-42-9 2-((Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-2-(5-methyl-7-oxo-2,4,5,7-tetrahydro-1H-furan[3,4-d][1,3]thiazin-2-yl)acetic acid 

Relevant articles and documents

Preparation method of cefdinir and novel intermediate compound thereof

The invention discloses a preparation method of cefdinir and a novel intermediate compound thereof. The cefdinir is prepared by adopting a method which is simpler, short in line and more environmentally friendly, and the prepared cefdinir is high in yield and higher in purity. The following reaction formula is adopted by the preparation method. The reaction formula is as shown in the specification.

Method for preparing cefdinir

The invention relates to a method for preparing cefdinir. The method includes condensing active ester of methoxyiminoacetic acid and 7.amino.3.vinyl.3.cephalosporin ring.4.carboxylate ester in the presence of organic alkali; carrying out ester hydrolysis reaction. The method has the advantages of few reaction steps, high yield and simplicity in post-treatment.

Method for synthesizing cefdinir

The invention relates to a method for synthesizing cefdinir. The method includes carrying out condensation reaction on cefdinir parent nuclei 7-AVCA and cefdinir side-chain active ester to obtain cefdinir with protecting groups; adding hydrogen chloride and catalysts into reaction liquid without separation on the reaction liquid and removing the protecting groups to obtain the cefdinir. The cefdinir parent nuclei 7-AVCA are used as raw materials. The method has the advantages that reaction for removing the protecting groups is directly carried out without separation on an intermediate product (the cefdinir with the protecting groups), accordingly, the cefdinir can be obtained under high-yield conditions, the yield can reach 85% at least, the method is short in synthetic reaction process route, and reagents are inexpensive and are low in cost.

Cefdinir synthesizing technology

The invention provides a cefdinir synthesizing technology. The technology comprises the steps that (Z)-2-(2-aminothiazole-4-yl)-2-acetoxyl imino thioacetic acid(S-2-benzothiazole)ester and 7-amino-3-vinyl-8-oxo-5-thia-1-azabicyalo[4.2.0]oct-2-alkene-2-carboxylic acid are subjected to condensation; acetyl protection is removed through hydrolysis, and a cefdinir finished product is finally obtained. The method for preparing the cefdinir has the advantages of being short in production cycle, high in yield, high in product quality and suitable for industrial production.

CEFDINIR synthesis process

Cefdinir preparation by synthesis of new key intermediates, isolable as variously solvated species complexed with thiophosphoric acid derivatives or with phosphoric acid derivatives.

Improved synthesis of Cefdinir and its polymorphic form, an antibacterial active pharmaceutical ingredient

New methods for the preparation of Cefdinir 1 and its polymorphic form Sesqui hydrate 1a are described. The synthesis of 2-mercaptobenzothiazolyl (Z)-2-(2-amino-4-thiazolyl)-2-acetoxyiminoacetate 4 was affected by using triphenylphosphine and triethylamine, and acylation of 7-amino-3-vinylcephem-4- carboxylic acid 5 followed by deprotection with K2CO3 in the presence of ammonium chloride in the same pot yielded crude Cefdinir. Purification of crude Cefdinir through resin and treatment of the resulting wet product with trifluoroacetic acid gave highly pure TFA salt of Cefdinir 6, which on neutralization afforded 1a in excellent yield. The impurity profiling of this compound has also been discussed. Copyright Taylor & Francis Group, LLC.

Novel compounds for the synthesis of Cefdinir

(Chemical Equation Presented) Preparation of two new compounds 2-mercapto-5-methyl-1,3,4-thiadiazolyl-(Z)-2-(2-amino-4-thiazolyl) -2-trityloxyiminoacetate (14) and 2-mercapto-5-methyl-1, 3,4-thiadiazolyl- (Z)-2-(2-amino-4-thiazolyl)-2-acetyloxyiminoacetate (12) and their use in the preparation of 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido]-3- vinylcephem-4-carboxylic acid, also known by the generic name Cefdinir (1) has been accomplished in a single step by coupling with 7-amino-3-vinylcephem-4- carboxylic acid (7) with purity of greater than 99% by HPLC.

Crystalline form of cefdinir cesium salt

Provided is the cesium salt of cefdinir, processes for its preparation and its use in the preparation of cefdinir.

Process for the preparation of cefdinir

The invention relates to processes for preparing cefdinir via its potassium and cesium salts.

CRYSTALLINE FORMS OF CEFDINIR POTASSIUM SALT

The present invention encompasses the solid state chemistry of cefdinir potassium salt.