Levofloxacin ethyl ester

Base Information

• Chemical Name: Levofloxacin ethyl ester
• CAS No.: 177472-30-9
• Molecular Formula: C20H24FN3O4
• Molecular Weight: 389.4207
• Hs Code.: 2934990002
• UNII: RXT0370X9X
• DSSTox Substance ID: DTXSID701103949
• Wikidata: Q27288330
• Mol file: 177472-30-9.mol

Synonyms:Levofloxacin ethyl ester;RXT0370X9X;Levofloxacin ethyl ester, (-)-;(S)-Ethyl 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylate;7H-Pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, ethyl ester, (3S)-;UNII-RXT0370X9X;SCHEMBL13502978;DTXSID701103949;Q27288330;LEVOFLOXACIN HEMIHYDRATE IMPURITY H [EP IMPURITY];(3S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid ethyl ester;7H-Pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, ethyl ester, (S)-;Levofloxacin Related Compound C;Levofloxacin Hemihydrate Impurity H;Ethyl (3S)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate

Chemical Property of Levofloxacin ethyl ester

Chemical Property:

• Vapor Pressure: 1.48E-12mmHg at 25°C
• Boiling Point: 559.6°C at 760 mmHg
• PKA: 7.37±0.42(Predicted)
• Flash Point: 292.3°C
• PSA: 64.01000
• Density: 1.36g/cm³
• LogP: 2.02540
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 389.17508442
• Heavy Atom Count: 28
• Complexity: 664

Purity/Quality:

99% ^*data from raw suppliers

LevofloxacinEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=CN2C(COC3=C2C(=CC(=C3N4CCN(CC4)C)F)C1=O)C
• Isomeric SMILES: CCOC(=O)C1=CN2[C@H](COC3=C2C(=CC(=C3N4CCN(CC4)C)F)C1=O)C
• Uses: Levofloxacin Ethyl Ester (Levofloxacin USP Related Compound C) is an impurity of Levofloxacin (L360000).

Technology Process of Levofloxacin ethyl ester

There total 7 articles about Levofloxacin ethyl ester 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: 83.7%

(S)-ethyl 3-(1-hydroxypropan-2-ylamino)-2-(2,3,5-trifluoro-4-(4-methylpiperazin-1-yl)benzoyl)acrylate (177472-28-5) → C20H24FN3O4 (177472-30-9)

Guidance literature:

With potassium carbonate; In water; at 140 ℃; for 4h;

Reference yield: 75.0%

ethanol (64-17-5) + ofloxacin (82419-36-1,83380-47-6) → ethyl (+/-)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate (107884-32-2,177472-30-9)

Guidance literature:

With sulfuric acid; for 48h; Reflux;

DOI:10.1007/s00044-011-9655-8

Reference yield:

ethyl 3-(dimethylamino)acrylate (924-99-2,1117-37-9,114894-59-6) → C20H24FN3O4 (177472-30-9)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / toluene / 4 h / 27 °C

2: triethylamine / 0.5 h / 20 °C / pH 5 - 6

3: 24 h / 120 °C

4: potassium carbonate / 16 h / 140 °C

With potassium carbonate; triethylamine; In toluene;

upstream raw materials:

(S)-ethyl 3-(1-hydroxypropan-2-ylamino)-2-(2,3,5-trifluoro-4-(4-methylpiperazin-1-yl)benzoyl)acrylate

ethyl 3-(dimethylamino)acrylate

2,3,4,5-tetrafluorobenzoyl chloride

ethyl α<(N,N-dimethylamino)methylene>-2,3,4,5-tetrafluoro-β-oxobenzenepropanoate

Downstream raw materials:

levofloxacin

Refernces

• 1、 -. "Preparation method of levofloxacin and intermediates thereof". Paragraph 0065-0072. . Retrieved 2021/03/30.
• 2、 Xu, Min,Zhang, Yu-Cui,Xu, Zhi-Hong,Zeng, Zheng-Zhi. "Crystal structure, biological studies of water-soluble rare earth metal complexes with an ofloxacin derivative". scheme or table. p. 324 - 332. Retrieved 2012/05/20.