13838-08-9

Basic information

• Product Name: azidamfenicol
• Synonyms: azidamfenicol;AZIAMPHENICOL, PHARMA;azidoamphenicol;2-Azido-N-[(1R,2R)-2-hydroxy-1-hydroxymethyl-2-(4-nitrophenyl)ethyl]acetamide;AzidoaMphenicol, LeukoMycin N
• CAS NO: 13838-08-9
• Molecular Formula: C₁₁H₁₃N₅O₅
• Molecular Weight: 295.254
• EINECS: 237-552-9
• Mol File: 13838-08-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 107°
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Ethyl Acetate (Slightly, Sonicated), Methanol (Slightly)
• CAS DataBase Reference: azidamfenicol(CAS DataBase Reference)
• NIST Chemistry Reference: azidamfenicol(13838-08-9)
• EPA Substance Registry System: azidamfenicol(13838-08-9)

Safety Data

• Hazardous Substances Data: 13838-08-9(Hazardous Substances Data)

Usage

Originator

Berlicetin-,Chauvin

Uses

Azidamfenicol is a semi-synthetic chloramphenicol in which the nitro moiety is replaced with a methylsulphone and the dichloroacetamide is replaced with azidoacetamide, first synthesised at Bayer in 1959. Azidamfenicol is a broad spectrum antibiotic with good activity against Gram negative and anaerobic bacteria. Azidamfenicol acts by binding to the 23S sub-unit of the 50S ribosome, inhibiting protein synthesis. Azidamfenicol has received little research attention with only a few literature citations.

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

Downstream Products

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

Relevant articles and documents

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.