(-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate

Base Information

• Chemical Name: (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate
• CAS No.: 110548-03-3
• Molecular Formula: C₁₅H₁₄F₃NO₄
• Molecular Weight: 329.276
• Mol file: 110548-03-3.mol

Synonyms:(-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate

Chemical Property of (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate

Chemical Property:

Purity/Quality:

>95% ^*data from raw suppliers

6,7,8-Trifluoro-1,4-dihydro-1-[(1S)-2-hydroxy-1-methylethyl]-4-oxo-3-quinolinecarboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 6,7,8-Trifluoro-1,4-dihydro-1-[(1S)-2-hydroxy-1-methylethyl]-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester is used in the synthesis of the drug Levofloxacin (L360000), which is a S-(-) form of Ofloxacin (O245750), an antibiotic used against gram-negative organisms.

Technology Process of (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate

There total 7 articles about (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate 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: 82.0%

(-)-ethyl 1,4-dihydro-1-[1(S)-(acetoxymethyl)ethyl]-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate (188058-77-7) → (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate (110548-03-3)

Guidance literature:

With potassium carbonate; In methanol; for 0.5h; Ambient temperature;

Reference yield: 62.0%

(+)-ethyl 2-<<<(S)-1-hydroxyprop-2-yl>amino>methylene>-3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate (110548-02-2) → (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate (110548-03-3)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide;

DOI:10.1016/j.bmcl.2007.11.110

Reference yield:

ethyl 3-(2,3,4,5-tetrafkuorophenyl)-3-oxopropanoate (94695-50-8) → (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate (110548-03-3)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic anhydride / 2 h / 110 °C

2: CH₂Cl₂ / 0.5 h / Ambient temperature

3: 59 percent / 50percent NaH / dimethylsulfoxide / 3 h / Ambient temperature

With sodium hydride; In dichloromethane; acetic anhydride; dimethyl sulfoxide;

DOI:10.1021/jm00395a017

upstream raw materials:

(+)-ethyl 2-<<<(S)-1-hydroxyprop-2-yl>amino>methylene>-3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate

(-)-ethyl 1,4-dihydro-1-[1(S)-(acetoxymethyl)ethyl]-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate

2,3,4,5-tetrafluorobenzoyl chloride

(+)-ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-[(1-acetoxyprop-2(S)-yl)amino]acrylate

Downstream raw materials:

levofloxacin

levofloxacin Q-acid

Refernces

• 1、 Kang, Soon Bang,Park, Seonhee,Kim, Yong Hae,Kim, Youseung. "An improved synthesis of levofloxacin". . p. 137 - 145. Retrieved 2007/10/03.