Desmethyl levofloxacin

Base Information

• Chemical Name: Desmethyl levofloxacin
• CAS No.: 117707-40-1
• Molecular Formula: C17H18 F N3 O4
• Molecular Weight: 347.346
• Hs Code.: 2934990002
• European Community (EC) Number: 808-725-1
• UNII: 88ZBA45NC8
• Nikkaji Number: J371.852B
• Wikidata: Q27269969
• ChEMBL ID: CHEMBL1459
• Mol file: 117707-40-1.mol

Synonyms:Desmethyl levofloxacin;117707-40-1;N-Desmethyl levofloxacin;Uing 4-255;N-Desmethyl ofloxacin, (S)-;N-Desmethyl levofloxacin, (-)-;DN-5455;UNII-88ZBA45NC8;88ZBA45NC8;(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(piperazin-1-yl)-7-oxo-7H-pyrido(1,2,3-de)(1,4)benzoxazine-6-carboxylic acid;7H-Pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid, 9-fluoro-2,3-dihydro-3-methyl-7-oxo-10-(1-piperazinyl)-, (3S)-;Levofloxacin impurity, N-desmethyl levofloxacin- [USP];Ofloxacin Impurity E;(3S)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-10-(1-piperazinyl)-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid;Demethyllevofloxacin;des-methyl levofloxacin;N-Desmethyllevofloxacin;CHEMBL1459;SCHEMBL5021672;CHEBI:167761;(2S)-7-fluoro-2-methyl-10-oxo-6-piperazin-1-yl-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid;RKL10081;AKOS040732957;HY-135389;CS-0112235;F19493;Q27269969;LEVOFLOXACIN HEMIHYDRATE IMPURITY B [EP IMPURITY];LEVOFLOXACIN IMPURITY, N-DESMETHYL LEVOFLOXACIN- [USP IMPURITY];(S)-9-FLUORO-3-METHYL-10-(PIPERAZIN-1-YL)-7-OXO-2,3-DIHYDRO-7H-PYRIDO(1,2,3-DE)(1,4)BENZOXAZINE-6-CARBOXYLIC ACID;(S)-9-fluoro-3-methyl-7-oxo-10-(piperazin-1-yl)-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid;(S)-9-fluoro-3-methyl-7-oxo-10-(piperazin-1-yl)-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylicacid;(s)-9-fluoro-3-methyl-7-oxo-10-(piperazin-1-yl)-3,7dihydro-2h-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid;7-luoro-2-methyl-10-oxo-6-piperazin-1-yl-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

Chemical Property of Desmethyl levofloxacin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.677
• Boiling Point: 600.714°C at 760 mmHg
• PKA: 5.19±0.40(Predicted)
• Flash Point: 317.101°C
• PSA: 83.80000
• Density: 1.517g/cm³
• LogP: 1.59560
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Aqueous Acid (Slightly, Sonicated), Aqueous Base (Slightly, Sonicated), DMSO (Sl
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 347.12813423
• Heavy Atom Count: 25
• Complexity: 607

Purity/Quality:

98%Min ^*data from raw suppliers

Levofloxacin Related Compound A United States Pharmacopeia (USP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCNCC4)F)C(=O)O
• Isomeric SMILES: C[C@H]1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCNCC4)F)C(=O)O
• Uses: A metabolite of Levofloxacin Desmethyl Levofloxacin is a degradation product of levofloxacin. A levofloxacin impurity with antibacterial properties.

Technology Process of Desmethyl levofloxacin

There total 6 articles about Desmethyl levofloxacin 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: 97.0%

piperazine (110-85-0) + levofloxacin Q-acid (100986-89-8) → S-(-)-9-fluoro-2,3-dihydro-3-methyl-10-(1-piperazinyl)-7-oxo-7H-pyrido-<1,2,3-de><1,4>benzoxazine-6-carboxylic acid (117707-40-1)

Guidance literature:

With nano iron oxide on ZrO₂ coated sulfonic acid; In water; for 0.483333h; Reflux;

DOI:10.2174/1570178615666171226162735

Reference yield: 83.0%

piperazine (110-85-0) + diethyl ether (60-29-7,927820-24-4) + levofloxacin Q-acid (100986-89-8) → S-(-)-9-fluoro-2,3-dihydro-3-methyl-10-(1-piperazinyl)-7-oxo-7H-pyrido-<1,2,3-de><1,4>benzoxazine-6-carboxylic acid (117707-40-1)

Guidance literature:

With pyridine; In ethanol; water;

Reference yield:

ethyl 3-(2,3,4,5-tetrafkuorophenyl)-3-oxopropanoate (94695-50-8) → S-(-)-9-fluoro-2,3-dihydro-3-methyl-10-(1-piperazinyl)-7-oxo-7H-pyrido-<1,2,3-de><1,4>benzoxazine-6-carboxylic acid (117707-40-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 0.5 h / 140 °C

1.2: 40 h / 140 °C

1.3: 96 h / 20 °C

2.1: potassium carbonate / N,N-dimethyl acetamide / 0.42 h / 160 °C / Microwave irradiation

3.1: water; sodium hydroxide / ethanol / 1 h / 20 °C

4.1: dimethyl sulfoxide / 16 h / 125 °C

With water; potassium carbonate; sodium hydroxide; In ethanol; N,N-dimethyl acetamide; dimethyl sulfoxide;

upstream raw materials:

levofloxacin

piperazine

diethyl ether

levofloxacin Q-acid

Downstream raw materials:

(S)-10-(4-(3-(benzylamino)-2-hydroxypropyl)piperazin-1-yl)-9-fluoro-3,7-dihydro-3-methyl-7-oxo-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

(S)-9-fluoro-3,7-dihydro-10-(4-(2-hydroxy-3-(phenylamino)propyl)piperazin-1-yl)-3-methyl-7-oxo-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

(S)-9-fluoro-3,7-dihydro-3-methyl-10-(4-((oxiran-2-yl)methyl)piperazin-1-yl)-7-oxo-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

levofloxacin

Refernces

• 1、 -. "ANTIBIOTIC RESISTANCE BREAKERS". Page/Page column 163. . Retrieved 2019/01/05.
• 2、 Guruswamy,Arul. "Synthesis, characterization, antimicrobial activity of novel n-substituted β-hydroxy amines and βhydroxy ethers contained chiral benzoxazine fluoroquinolones". . p. 86 - 93. Retrieved 2013/08/22.