128438-00-6

Basic information

• Product Name: ethyl (2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate
• Synonyms: ethyl (2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate
• CAS NO: 128438-00-6
• Molecular Weight: 457.553
• Mol File: 128438-00-6.mol

Chemical Properties

• CAS DataBase Reference: ethyl (2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate(128438-00-6)
• EPA Substance Registry System: ethyl (2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate(128438-00-6)

Safety Data

• Hazardous Substances Data: 128438-00-6(Hazardous Substances Data)

Upstream product

• 76-83-5 trityl chloride 
• 64485-82-1 (Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate 
• 76-84-6 triphenylmethyl alcohol 

Downstream Products

• 128438-01-7 (Z)-2-(2-aminothiazol-4-yl)-2-(triphenylmethoxyimino)acetic acid 
• 454472-30-1 ethyl (Z)-2-(4-thiazolyl)-2-(trityloxyimino)acetate 
• 73151-05-0 (Z)-2-(4-thiazolyl)-2-(trityloxyimino)acetic acid 
• 454472-41-4 diphenylmethyl 7β-[(Z)-2-(thiazol-4-yl)-2-(trityloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate 
• 189449-52-3 (Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetic acid 
• 189449-54-5 (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylate diphenylmethyl ester 
• 189449-55-6 (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-mercapto-3-cephem-4-carboxylate diphenylmethyl ester 
• 189449-58-9 (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-[3-(N-tert-butoxycarbonylaminoethylthiomethyl)pyrid-4-ylthio]-3-cephem-4-carboxylate diphenylmethyl ester 

Relevant articles and documents

PROCESS FOR PREPARING 2-AMINOTHIAZOL-4-YL-ACETIC ACID DERIVATES

The invention provides a process for preparing a (2-aminothiazol-4-yl)-triarylmethyloxy- iminoacetic acid of the formula (I) or an ester thereof of the formula (II) wherein R1, R2 and R3 independently are optionally substi

Discovery of RWJ-54428 (MC-02,479), a new cephalosporin active against resistant gram-positive bacteria

The discovery of RWJ-54428 (MC-02,479), a new cephalosporin displaying promising activity against sensitive and resistant Gram-positive bacteria, is described. Progressive structural modification from the previously reported 3-phenylthiocephem MC-02,331 afforded an overall increase in potency against MRSA while retaining other key properties such as acceptable solubility and serum binding. Evaluation of the in vitro potency and in vivo efficacy of a series of closely related compounds resulted in selection of RWJ-54428 (MC-02,479) for further studies.

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.

Process for cephem prodrug esters

A process for the selective formation of oximino o-protected derivatives of lower alkyl 2-(2-aminothiazol-4-yl)-2-oximinoacetates, and their use in the acylation of 7-amino-cephalosporin compounds is disclosed.