69689-86-7

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-2-[2-(Tritylamino)thiazol-4-yl]-2-(trityloxyimino)acetic Acid Ethyl Ester is used as a key intermediate in the synthesis of Cefdinir (C242670), a third-generation cephalosporin antibiotic. It is employed for its ability to facilitate the formation of the desired antibiotic structure, contributing to the development of effective treatments for bacterial infections.
As an intermediate in the synthesis of other pharmaceuticals:
Due to its unique molecular structure, (Z)-2-[2-(Tritylamino)thiazol-4-yl]-2-(trityloxyimino)acetic Acid Ethyl Ester may also be used in the synthesis of other pharmaceutical compounds, potentially leading to the discovery of new drugs with improved properties and therapeutic effects. Its versatility in chemical reactions makes it a valuable component in the development of various medications.

Upstream product

• 66508-93-8 ethyl 2-(hydroxyimino)-3-oxybutyrate 
• 66338-95-2 ethyl 4-chloro-2-hydroxyimino-3-oxo-butyrate 
• 141-97-9 ethyl acetoacetate 
• 76-83-5 trityl chloride 
• 64485-82-1 (Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate 

Downstream Products

• 68786-47-0 (Z)-2-(trityloxyimino)-2-(2-tritylamino-4-thiazolyl)acetic acid 
• 123201-39-8 diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino]-3-vinyl-3-cephem-4-carboxylate 
• 128454-32-0 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid 
• 91832-40-5 cefdinir 

Relevant academic research and scientific papers

CARBACEPHEM BETA-LACTAM ANTIBIOTICS

Carbacephem β-lactam antibiotics having structure (I) are disclosed, including stereoisomers, pharmaceutically acceptable salts, esters and prodrugs thereof, wherein Ar2, X, R1 and R2 are as defined herein. The compounds are useful for the treatment of bacterial infections, in particular those caused by methicillin-resistant Staphylococcus spp.

CARBACEPHEM BETA-LACTAM ANTIBIOTICS

Carbacephem β-lactam antibiotics having chemical structures (I) and (II) are disclosed: including stereoisomers, pharmaceutically acceptable salts, esters and prodrugs thereof, wherein Ar2, R1, R2 and R6 are as defined herein. The compounds are useful for the treatment of bacterial infections, in particular those caused by methicillin-resistant Staphylococcus spp.

CARBACEPHEM β-LACTAM ANTIBIOTICS

Carbacephem -lactam antibiotics having structure (I) are disclosed, including stereoisomers, pharmaceutically acceptable salts, esters and prodrugs thereof, wherein Ar1, Ar2, R1 and R2 are as defined herein. The compounds are useful for the treatment of bacterial infections, in particular those caused by methicillin-resistant Staphylococcus spp.

Stable bioavailable crystalline form or cefdinir and a process for the preparation thereof

The present invention relates to a stable and bioavailable crystalline form of a third generation cephalosporin antibiotic, cefdinir and a process for the preparation thereof. The present invention also relates to a pharmaceutical composition containing the novel crystalline cefdinir, useful in the treatment of maladies such as bacterial infections.

An alternative procedure for preparation of cefdinir

Cefdinir, a broad spectrum third-generation cephalosporin for oral administration, was prepared by the following synthetic pathway: synthesis of diphenylmethyl 7β-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride from 7-aminocephalosporanic acid (7-ACA), preparation of sodium 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino) acetate from ethyl acetoacetate, coupling of both intermediaries to obtain diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino-3- vinyl-3-cephem-4-carboxylate and final cleavage of trityl and diphenylmethyl protective groups. This procedure allows to obtain better yields of cefdinir and to avoid the use of diketene during the synthesis of this antibiotic by the previously reported method.

Synthesis of HR 916 K: An efficient route to the pure diastereomers of the 1-(pivaloyloxy)ethyl esters of cephalosporins

HR 916 K (5), the 1-(S)-(pivaloyloxy)ethyl prodrug ester of the cephalosporin cefdaloxime, exhibits a significantly higher oral bioavailability than the 1-(R) diastereomer HR 916 J. An efficient synthesis of HR 916 K was developed. The separation of the diastereomers was achieved by precipitation of the 1-(R)-hydrochloride 9 followed by crystallization of the 1-(S)-amine 10 (de > 96%). The 1-(R) diastereomer 9 was recycled by acidic saponification or enzymatic cleavage to AMCA (7). The amine 10 was acylated with mercaptobenzothiazole thioesters or mixed anhydrides, prepared from carboxylic acids 13 and 14, in almost quantitative yield. Deprotection of the oxime and formation of the tosylate proceeded in one step. Using thioester 18, we obtained HR 916 K (5) from AMCA (7) in 42% yield. VCH Verlagsgesellschaft mbH, 1996.