Benzyl-7-(4-{(5S)-5-{(acetylamino)methyl}-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate

Base Information

• Chemical Name: Benzyl-7-(4-{(5S)-5-{(acetylamino)methyl}-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate
• CAS No.: 444335-21-1
• Molecular Formula: C₃₂H₂₇F₂N₃O₆
• Molecular Weight: 587.58
• Mol file: 444335-21-1.mol

Synonyms:

Chemical Property of Benzyl-7-(4-{(5S)-5-{(acetylamino)methyl}-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl-7-(4-{(5S)-5-{(acetylamino)methyl}-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate

There total 9 articles about Benzyl-7-(4-{(5S)-5-{(acetylamino)methyl}-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate 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:

1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-3-quinoline-carboxylic acid (130579-27-0) → Benzyl-7-(4-{(5S)-5-{(acetylamino)methyl}-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate (444335-21-1)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 0 - 20 °C

2: 20 °C

3: Pd(PPh₃)2Cl₂; aq. K₂HPO₄ / 1,2-dimethoxy-ethane / 90 °C

4: TFA / CH₂Cl₂

5: pyridine

With pyridine; bis-triphenylphosphine-palladium(II) chloride; dipotassium hydrogenphosphate; trifluoroacetic acid; In 1,2-dimethoxyethane; dichloromethane;

DOI:10.1016/j.bmcl.2003.07.021

Reference yield:

tert-butyl (S)-((3-(4-bromo-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl)carbamate (444335-18-6) → Benzyl-7-(4-{(5S)-5-{(acetylamino)methyl}-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate (444335-21-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: EtMgBr; TMEDA / tetrahydrofuran / -50 °C

1.2: BuLi / tetrahydrofuran; hexane

2.1: Pd(PPh₃)2Cl₂; aq. K₂HPO₄ / 1,2-dimethoxy-ethane / 90 °C

3.1: TFA / CH₂Cl₂

4.1: pyridine

With pyridine; bis-triphenylphosphine-palladium(II) chloride; dipotassium hydrogenphosphate; N,N,N,N,-tetramethylethylenediamine; ethylmagnesium bromide; trifluoroacetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1016/j.bmcl.2003.07.021

Reference yield:

3-Nitro-benzenesulfonic acid (R)-3-(4-bromo-3-fluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester (444335-17-5) → Benzyl-7-(4-{(5S)-5-{(acetylamino)methyl}-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate (444335-21-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: aq. NH₄OH / acetonitrile; methanol / 80 °C

2.1: EtMgBr; TMEDA / tetrahydrofuran / -50 °C

2.2: BuLi / tetrahydrofuran; hexane

3.1: Pd(PPh₃)2Cl₂; aq. K₂HPO₄ / 1,2-dimethoxy-ethane / 90 °C

4.1: TFA / CH₂Cl₂

5.1: pyridine

With pyridine; bis-triphenylphosphine-palladium(II) chloride; ammonium hydroxide; dipotassium hydrogenphosphate; N,N,N,N,-tetramethylethylenediamine; ethylmagnesium bromide; trifluoroacetic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; acetonitrile;

DOI:10.1016/j.bmcl.2003.07.021

upstream raw materials:

acetic anhydride

1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-3-quinoline-carboxylic acid

tert-butyl (S)-((3-(4-bromo-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl)carbamate

3-Nitro-benzenesulfonic acid (R)-3-(4-bromo-3-fluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester