azidamfenicol

Base Information

• Chemical Name: azidamfenicol
• CAS No.: 13838-08-9
• Molecular Formula: C11H13 N5 O5
• Molecular Weight: 295.255
• Hs Code.: 2929909090
• European Community (EC) Number: 237-552-9
• UNII: 40257685LM
• DSSTox Substance ID: DTXSID90160647
• Nikkaji Number: J8.449B
• Wikipedia: Azidamfenicol
• Wikidata: Q425029
• NCI Thesaurus Code: C72712
• Metabolomics Workbench ID: 154117
• ChEMBL ID: CHEMBL3989525
• Mol file: 13838-08-9.mol

Synonyms:Acetamide,2-azido-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [R-(R*,R*)]-;Acetamide, 2-azido-N-[b-hydroxy-a-(hydroxymethyl)-p-nitrophenethyl]-,D-threo-(-)- (8CI); Azidamfenicol; Azidamphenicol; Azidoamphenicol;D-(-)-threo-1-p-Nitrophenyl-2-azidoacetylamino-1,3-propanediol; Leukomycin N

Chemical Property of azidamfenicol

Chemical Property:

• Melting Point: 107°
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 165.13000
• Density: g/cm³
• LogP: 0.78246
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Ethyl Acetate (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 295.09166853
• Heavy Atom Count: 21
• Complexity: 412

Purity/Quality:

98%Min ^*data from raw suppliers

Azidamfenicol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C(CO)NC(=O)CN=[N+]=[N-])O)[N+](=O)[O-]
• Isomeric SMILES: C1=CC(=CC=C1[C@H]([C@@H](CO)NC(=O)CN=[N+]=[N-])O)[N+](=O)[O-]
• Recent EU Clinical Trials: A multicenter, double-blind, randomized, parallel arm comparative study for the assessment of the safety and efficacy of azidamfenicol eye drops (Thilocof?/FARMEX) versus tobramycine eye drops (Τobrex?/Alcon) in the treatment of patients with infections of the outer layers of the eye.
• 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.
• Therapeutic Function: Antibiotic

Technology Process of azidamfenicol

There total 13 articles about azidamfenicol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

Methyl azidoacetate (1816-92-8) + (4R,5R)-5-(4-nitrophenyl)-4-hydroxymethyl-1,3-oxazolidin-2-one (294637-52-8) → Azidamfenicol (13838-08-9)

Guidance literature:

(4R,5R)-5-(4-nitrophenyl)-4-hydroxymethyl-1,3-oxazolidin-2-one; With sodium hydroxide; for 0.5h; Reflux;

Methyl azidoacetate; In methanol; at 0 - 40 ℃; for 9h;

DOI:10.1021/acs.joc.0c02181

Reference yield: 64.0%

N-((1R,2R)-1-(4-aminophenyl)-1,3-dihydroxypropan-2-yl)-2-azidoacetamide → Azidamfenicol (13838-08-9)

Guidance literature:

With ethylenediaminetetraacetic acid; potassium peroxymonosulfate; sodium hydrogencarbonate; sodium hydroxide; In water; acetone; at 0 - 25 ℃; for 0.025h;

DOI:10.1021/acs.joc.1c01124

Reference yield:

4-nitrobenzaldehdye (555-16-8) → Azidamfenicol (13838-08-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: C₂₉H₂₈F₆N₄O₂ / chloroform / 60 h / -60 °C

2.1: potassium hydroxide / water; tetrahydrofuran / 0.17 h / 0 °C / 7500.75 Torr

3.1: 1H-imidazole / tetrahydrofuran / 0.13 h / 70 °C / 7500.75 Torr

4.1: sodium tetrahydroborate / methanol / 4.33 h / 20 °C

5.1: sodium hydroxide / 0.5 h / Reflux

5.2: 9 h / 0 - 40 °C

With 1H-imidazole; sodium tetrahydroborate; C₂₉H₂₈F₆N₄O₂; potassium hydroxide; sodium hydroxide; In tetrahydrofuran; methanol; chloroform; water;

DOI:10.1021/acs.joc.0c02181

upstream raw materials:

azidoacetonitrile

(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

2-azido-acetamide

2-azidoacetyl chloride

Downstream raw materials:

(2S,3R) 2-amino-1-(4-aminophenyl)-1,3-propanediol

2-amino-1-(4-nitrophenyl)propane-1,3-diol

Refernces

• 1、 Liu, Jinxin,Li, Yaling,Ke, Miaolin,Liu, Minjie,Zhan, Pingping,Xiao, You-Cai,Chen, Fener. "Unified Strategy to Amphenicol Antibiotics: Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, and (+)-Thiamphenicol and Its (+)-3-Floride". . p. 15360 - 15367. Retrieved 2020/11/30.