Levonadifloxacin

Base Information

• Chemical Name: Levonadifloxacin
• CAS No.: 154357-42-3
• Molecular Formula: C19H21 F N2 O4
• Molecular Weight: 360.38
• UNII: 8WHH66L098
• DSSTox Substance ID: DTXSID70165599
• Nikkaji Number: J281.731D
• Wikidata: Q27117310
• NCI Thesaurus Code: C83879
• Metabolomics Workbench ID: 55721
• ChEMBL ID: CHEMBL190561
• Mol file: 154357-42-3.mol

Synonyms:(12S)-8-(4-((2S)-2-aminopropanoyl)oxypiperidin-1-yl)-7-fluoro-12-methyl-4-oxo-1-azatricyclo(7.3.1.05,13)trideca-2,5,7,9(13)-tetraene-3-carboxylic acid;(S)-(-)-nadifloxacin;alalevonadifloxacin;EMROK;EMROK O;L-Alanine, 1-((5S)-2-carboxy-9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo(ij)quinolizin-8-yl)-4-piperidinyl ester;levonadifloxacin;WCK 2349

Chemical Property of Levonadifloxacin

Chemical Property:

• PSA: 82.77000
• Density: 1.46
• LogP: 2.37210
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 360.14853532
• Heavy Atom Count: 26
• Complexity: 631

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-(-)-Nadifloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2=C3N1C=C(C(=O)C3=CC(=C2N4CCC(CC4)O)F)C(=O)O
• Isomeric SMILES: C[C@H]1CCC2=C3N1C=C(C(=O)C3=CC(=C2N4CCC(CC4)O)F)C(=O)O
• Uses: (S)-(-)-Nadifloxacin is an anti-bacterial agent against multidrug-resistant Staphylococcus aureus. Also, it is derived from 6-Fluoro-2-methylquinoline (F595900), which is an quinoline derivative, a highly potent thrombin receptor antagonist.

Technology Process of Levonadifloxacin

There total 5 articles about Levonadifloxacin 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: 74.0%

4-HYDROXYPIPERIDINE (5382-16-1) + (S)-(O-B)-diacetoxy-(8,9-difluoro-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxy)borane → S-(-)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid (154357-42-3,81962-84-7)

Guidance literature:

In acetonitrile; at 50 - 60 ℃; for 4h;

DOI:10.1248/cpb.44.642

Reference yield: 36.0%

4-HYDROXYPIPERIDINE (5382-16-1) + (S)-8-Bromo-9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid → S-(-)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid (154357-42-3,81962-84-7)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; at 140 ℃; for 5h;

DOI:10.1248/cpb.44.642

Reference yield:

nadifloxacin (124858-35-1,81962-84-7) → R-(+)-9-fluoro-8-(4-hydroxypiperidin-1-yl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid (81962-84-7) + S-(-)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid (154357-42-3,81962-84-7)

Guidance literature:

With Lux-cellulose-2 (cellulose tris(3-chloro-4-methyl phenyl carbamate)) column; In ethanol; hexane; acetic acid; diethylamine; at 35 ℃; Solvent; Temperature; Resolution of racemate;

DOI:10.1002/chir.22861

upstream raw materials:

4-HYDROXYPIPERIDINE

5-bromo-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

(S)-5-Bromo-6-fluoro-2-methyl-1,2,3,4-tetrahydro-quinoline

nadifloxacin

Downstream raw materials:

(2'S,5S)-9-fluoro-6,7-dihydro-8-(4-(N-tert-butoxycarbonyl-L-alaninyl-oxy)-piperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid

Refernces

• 1、 Hashimoto, Koji,Okaichi, Yoshihiko,Nomi, Daisuke,Miyamoto, Hisashi,Bando, Masahiko,Kido, Masaru,Fujimura, Tsutomu,Furuta, Takuya,Minamikawa, Jun-Ichi. "A practical synthesis of (S)-(-)-nadifloxacin: Novel acid-catalyzed racemization of tetrahydroquinaldine derivative". . p. 642 - 645. Retrieved 2007/10/03.