13838-08-9

Usage

Uses

Used in Pharmaceutical Industry:
Azidamfenicol is used as a broad-spectrum antibiotic for treating bacterial infections caused by Gram-negative and anaerobic bacteria. Its application is particularly valuable in scenarios where conventional antibiotics may be less effective or where bacterial resistance is a concern.
Used in Research and Development:
Due to its unique structure and mechanism of action, azidamfenicol serves as a valuable compound in the field of research and development. It can be utilized to study the interactions between antibiotics and bacterial ribosomes, as well as to develop new drugs with improved efficacy and reduced resistance potential.
Used in Veterinary Medicine:
Azidamfenicol is also employed in veterinary medicine as an antibiotic to treat bacterial infections in animals. Its broad-spectrum activity makes it a useful tool for managing various bacterial infections in livestock and pets, contributing to the overall health and well-being of the animals.

Originator

Berlicetin-,Chauvin

Manufacturing Process

21.2 g of D-(-)-threo-1-p-nitrophenyl-2-aminopropane-1,3-diol are stirred with 10 g of azidoacetonitrile (B.P. 68°C/25 mm) in a mixture of 125 ml of methanol and 125 ml of water at 30-40°C for a few days. The mixture is filtered off from a little undissolved base and the solvent is distilled in vacuo. The residue is treated with a little normal hydrochloric acid until acid to Congo red and extracted with ethylacetate. By evaporating the solvent and recrystallizing the residue from ethylene chloride is obtained D-(-)-threo-1-pnitrophenyl- 2-azidoacetylamino-propane-1,3-diol, M.P. 107°C.

Therapeutic Function

Antibiotic

InChI:InChI=1/C11H13N5O5/c12-15-13-5-10(18)14-9(6-17)11(19)7-1-3-8(4-2-7)16(20)21/h1-4,9,11,17,19H,5-6H2,(H,14,18)/t9-,11-/m1/s1

Upstream product

• 57707-64-9 azidoacetonitrile 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 1816-91-7 2-azido-acetamide 
• 30426-58-5 2-azidoacetyl chloride 
• 35530-10-0 [(1R,2R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol] hydrochloride 
• 1816-92-8 Methyl azidoacetate 
• 294637-50-6 ethyl (4S,5R)-5-(4-nitrophenyl)-2-oxooxazolidine-4-carboxylate 
• 294637-52-8 (4R,5R)-5-(4-nitrophenyl)-4-hydroxymethyl-1,3-oxazolidin-2-one 
• 555-16-8 4-nitrobenzaldehdye 
• 2663-91-4 (1R,2R)-(-)-2-amino-1-(4-aminophenyl)-1,3-propanediol 

Downstream Products

• 2663-91-4 (2S,3R) 2-amino-1-(4-aminophenyl)-1,3-propanediol 
• 119-62-0 2-amino-1-(4-nitrophenyl)propane-1,3-diol 

Relevant academic research and scientific papers

Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol

A unified strategy for an efficient and high diastereo- and enantioselective synthesis of (-)-chloramphenicol, (-)-azidamphenicol, (+)-thiamphenicol, and (+)-florfenicol based on a key catalytic syn-selective Henry reaction is reported. The stereochemistry of the ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol was first explored to forge a challenging syn-2-amino-1,3-diol structure unit with vicinal stereocenters with excellent stereocontrol. Multistep continuous flow manipulations were carried out to achieve the efficient asymmetric synthesis of this family of amphenicol antibiotics.

Unified Strategy to Amphenicol Antibiotics: Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, and (+)-Thiamphenicol and Its (+)-3-Floride

The asymmetric synthesis of (-)-chloramphenicol, (-)-azidamphenicol, and (+)-thiamphenicol and its (+)-3-floride, (+)-florfenicol, is reported. This approach toward the amphenicol antibiotic family features two key steps: (1) a cinchona alkaloid derived urea-catalyzed aldol reaction allows highly enantioselective access to oxazolidinone gem-diesters and (2) a continuous flow diastereoselective decarboxylation of thermally stable oxazolidinone gem-diesters to form the desired trans-oxazolidinone monoesters with two adjacent stereocenters that provide the desired privileged scaffolds of syn-vicinal amino alcohols in the amphenicol family.