143183-03-3

Basic information

• Product Name: (Benzothiazol-2-yl)-(Z)-2-trityloxyimino-2-(2-aminothiazole-4-yl)-thioacetate
• Synonyms: S-2-BENZOTHIAZOLYL(Z)-2-(2-AMINOTHIAZOL-4-YL)-2-TRITYLOXYIMINOTHIOACETATE;(Benzothiazol-2-yl)-(Z)-2-Trityimino-2-(2-Aminothiazol-4-yl)Thioac etate;2-mercaptobenzothiazolyl (z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetate;2-Mercaptobenzothiazolyl-(Z)-2-(2-Aminothiazol-4-Yl)-2-Trityloxyiminoacetate;S-2-BENZOTHIAZOLYL(Z)-2-(2-AMINOTHIAZOL-4-YL)-2-TRITYLOXYIMINOTHIOACETATE (BAEM);S-2-BENZOTHIAZOLYL(Z)-2-(2-AMINOTHIAZOL-4-YL)-2-TRITYLOXYIMINOTHIOACETATE(BAEM);(benzothiazol-2-yl)-(Z)-2-(2-aminothiazol-4-yl)thioacetate;2-mercaptobenzothiazolyl (z)-(2-aminothiazol-4-yl)-2-trityloxyiminoacetate
• CAS NO: 143183-03-3
• Molecular Formula: C₃₁H₂₂N₄O₂S₃
• Molecular Weight: 578.73
• Mol File: 143183-03-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 767.438 °C at 760 mmHg
• Flash Point: 417.932 °C
• Appearance: /
• Density: 1.367 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.721
• PKA: 0.90±0.10(Predicted)
• CAS DataBase Reference: (Benzothiazol-2-yl)-(Z)-2-trityloxyimino-2-(2-aminothiazole-4-yl)-thioacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (Benzothiazol-2-yl)-(Z)-2-trityloxyimino-2-(2-aminothiazole-4-yl)-thioacetate(143183-03-3)
• EPA Substance Registry System: (Benzothiazol-2-yl)-(Z)-2-trityloxyimino-2-(2-aminothiazole-4-yl)-thioacetate(143183-03-3)

Safety Data

• Hazardous Substances Data: 143183-03-3(Hazardous Substances Data)

Usage

General Description

The chemical compound "(Benzothiazol-2-yl)-(Z)-2-trityloxyimino-2-(2-aminothiazole-4-yl)-thioacetate" is a complex organic molecule with a number of functional groups. It contains benzothiazole and amino-thiazole rings, as well as a trityloxyimino and thioacetate groups. The compound also features a Z-configuration, indicating a specific arrangement of the trityloxyimino and amino-thiazole groups. (Benzothiazol-2-yl)-(Z)-2-trityloxyimino-2-(2-aminothiazole-4-yl)-thioacetate may have potential applications in pharmaceuticals, materials science, or organic synthesis, due to its diverse and potentially valuable chemical structure.

InChI:InChI=1/C31H22N4O2S3/c32-29-33-25(20-38-29)27(28(36)40-30-34-24-18-10-11-19-26(24)39-30)35-37-31(21-12-4-1-5-13-21,22-14-6-2-7-15-22)23-16-8-3-9-17-23/h1-20H,(H2,32,33)/b35-27-

Upstream product

• 64485-82-1 (Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate 
• 76-83-5 trityl chloride 
• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 128438-01-7 (Z)-2-(2-aminothiazol-4-yl)-2-(triphenylmethoxyimino)acetic acid 

Downstream Products

• 91832-40-5 cefdinir 
• 865411-26-3 N,N'-dicyclohexylethane-1,2-diamine salt of 7β-[2-(2-amino-4-thiazolyl)-2-((Z)-hydroxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid 
• 152401-10-0 (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-trityloxyimino]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (S)-1-(2,2-dimethyl-propionyloxy)-ethyl ester 

Relevant articles and documents

Studies on Anti-MRSA parenteral cephalosporins I. Synthesis and antibacterial activity of 7

In order to improve the antibacterial activity of cefozopran (CZOP) against methicillin-resistant Staphylococcus aureus (MRSA), we initiated chemical modification to introduce a 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-hydroxyimino acetyl group at the C-7 position and a 3- or 6-substituted imidazo[1,2-b]pyridazinium or 5-substituted imidazo[1,2-a]pyridinium group at the C-3' position. Although this approach successfully enhanced the anti-MRSA activity of CZOP two to eight times, a slight decrease in the activity against Gram-negative bacteria including Pseudomonas aeruginosa was involved. Among the novel derivatives, 3-(6-aminoimidazo [1,2-b]pyridazinium-1-yl) methyl-7β-[2-(5-amino -1,2,4-thiadiazol-3-yl) -2(Z)-hydroxyiminoacetamidol]-3-cephem-4-carboxylate (44a) showed an excellent balance of activity against MRSA and Gram-negative bacteria.

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.