68786-47-0

Usage

Uses

Intermediate in the preparation of Cefdinir (C242670).

InChI:InChI=1/C43H33N3O3S/c47-40(48)39(46-49-43(35-25-13-4-14-26-35,36-27-15-5-16-28-36)37-29-17-6-18-30-37)38-31-50-41(44-38)45-42(32-19-7-1-8-20-32,33-21-9-2-10-22-33)34-23-11-3-12-24-34/h1-31H,(H,44,45)(H,47,48)/b46-39+

Upstream product

• 69689-86-7 ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino)acetate 
• 76-83-5 trityl chloride 
• 128438-01-7 (Z)-2-(2-aminothiazol-4-yl)-2-(triphenylmethoxyimino)acetic acid 
• 64485-82-1 (Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate 
• 66338-96-3 2-(2-Amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetic acid 

Downstream Products

• 214341-23-8 (7R)-7-[(Z)-2-(2-N-triphenylmethylaminothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-[2,4-bis(chloromethyl)phenylthio]-3-cephem-4-carboxylate, 4-methoxybenzyl ester 
• 220779-47-5 (6R,7R)-3-((Z)-2-Isoxazol-5-yl-vinyl)-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 220779-91-9 (6R,7R)-3-[(Z)-2-(3-Chloro-isoxazol-5-yl)-vinyl]-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 220779-81-7 (6R,7R)-3-[(Z)-2-(3-Methoxy-isoxazol-5-yl)-vinyl]-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 

Relevant academic research and scientific papers

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.

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.

Structural modifications and biological evaluation of 3-isoxazolylvinylcephalosporins

Structural modifications and biological evaluations of 3-isoxazolylvinylcephalosporins (I) were performed. The replacement of a hydrogen atom at the 7-aminothiazole group by a chlorine resulted in an improvement of the activity against resistant Gram-posi

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.