Levofloxacin carboxylic acid Chemical Properties

Melting point:

>300 °C (lit.)

Boiling point:

459.2±45.0 °C(Predicted)

Density 

1.61±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly)

pka

4.87±0.40(Predicted)

color 

White

optical activity

[α]20/D -64°, c = 1% in DMSO

InChI

InChI=1S/C13H9F2NO4/c1-5-4-20-12-9(15)8(14)2-6-10(12)16(5)3-7(11(6)17)13(18)19/h2-3,5H,4H2,1H3,(H,18,19)/t5-/m0/s1

InChIKey

NVKWWNNJFKZNJO-YFKPBYRVSA-N

SMILES

O1C2=C(F)C(F)=CC3C(=O)C(C(O)=O)=CN(C2=3)[C@@H](C)C1

CAS DataBase Reference

100986-89-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36/37/3

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

Levofloxacin carboxylic acid Usage And Synthesis

Chemical Properties

White Solid

Uses

Levofloxacin intermediate.

Definition

ChEBI: Ofloxacin impurity a is a member of quinolines.

Synthesis

Levofloxacin carboxylic acid was synthesized using ethyl (S)-9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate as starting material in the following steps: 1. to the residue after recovery of DMF was added acetic acid followed by 65 mL of water at room temperature and mixed with stirring. 2. sulfuric acid was slowly added dropwise, and when the dropwise addition was complete, it was heated to reflux and kept at reflux for 1 hour. 3. upon completion of the reaction, cooled to room temperature and subjected to filtration. 4. The filter cake was washed with 65 mL of water and subsequently dried to give 43.98 g of levodicyclic acid, the content of which was determined to be 96.22%. 5. The acetic acid was spun back through acetic acid and spun to dryness. 6. The filtrate was washed with water and filtered again to give 4.81 g of levulinic acid at 61.28%. 7. The recycled water and acetic acid can be recycled separately to minimize waste discharge and reduce raw material costs. 8. For the synthesis of tetrafluorobenzoyl chloride, the total yield after four steps was 87%.

References

[1] Patent: EP368410, 1990, A3
[2] Chemical and pharmaceutical bulletin, 1987, vol. 35, # 5, p. 1896 - 1902
[3] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 23, p. 4213 - 4216
[4] Patent: WO2006/48889, 2006, A1. Location in patent: Page/Page column 18
[5] Patent: US4985557, 1991, A

Levofloxacin carboxylic acid(100986-89-8)Related Product Information

• Folic acid
• Methyl acetate
• Tribenuron methyl
• 2,6-Lutidine
• Levofloxacin
• Azamethiphos
• 2-Chloro-5-chloromethylpyridine
• Oxygen-fluorine acid
• Chromium picolinate
• 2,4,6-Collidine
• Methyl salicylate
• 2-chloro-6-trichloromethylpyridine
• 4-Methylpyridine
• Ethyl 2-(Chlorosulfonyl)acetate
• Kresoxim-methyl
• Thiophanate-methyl
• Citric acid
• METSULFURON METHYL