(S)-6-(3-chloro-2-fluorobenzyl)-5-hydroxy-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Base Information

• Chemical Name: (S)-6-(3-chloro-2-fluorobenzyl)-5-hydroxy-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• CAS No.: 1333141-31-3
• Molecular Formula: C₂₂H₂₁ClFNO₅
• Molecular Weight: 433.864
• Mol file: 1333141-31-3.mol

Synonyms:(S)-6-(3-chloro-2-fluorobenzyl)-5-hydroxy-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property of (S)-6-(3-chloro-2-fluorobenzyl)-5-hydroxy-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-6-(3-chloro-2-fluorobenzyl)-5-hydroxy-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

There total 10 articles about (S)-6-(3-chloro-2-fluorobenzyl)-5-hydroxy-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 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: 24.0%

(S)-6-(3-chloro-2-fluorobenzyl)-1-(1-hydroxy-3-methylbutan-2-yl)-5-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1333141-32-4) → (S)-6-(3-chloro-2-fluorobenzyl)-5-hydroxy-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1333141-31-3)

Guidance literature:

(S)-6-(3-chloro-2-fluorobenzyl)-1-(1-hydroxy-3-methylbutan-2-yl)-5-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With boron tribromide; In dichloromethane; at -40 - 20 ℃;

With water; In dichloromethane;

DOI:10.1016/j.bmc.2011.06.020

Reference yield:

methyl 3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoate (1333140-87-6) → (S)-6-(3-chloro-2-fluorobenzyl)-5-hydroxy-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1333141-31-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium hydroxide / tetrahydrofuran; water / 3 h / 50 °C

1.2: pH 2

2.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 20 °C

2.2: 50 °C

3.1: tetrahydrofuran / 3 h / 50 °C

4.1: tetrahydrofuran / 50 °C

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 60 - 90 °C

6.1: methanol; water / 20 h / Reflux

6.2: pH 2

7.1: boron tribromide / dichloromethane / -40 - 20 °C

With boron tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.06.020

Reference yield:

3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoic acid (1333140-88-7) → (S)-6-(3-chloro-2-fluorobenzyl)-5-hydroxy-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1333141-31-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 20 °C

1.2: 50 °C

2.1: tetrahydrofuran / 3 h / 50 °C

3.1: tetrahydrofuran / 50 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 60 - 90 °C

5.1: methanol; water / 20 h / Reflux

5.2: pH 2

6.1: boron tribromide / dichloromethane / -40 - 20 °C

With boron tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.06.020

upstream raw materials:

methyl 3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoate

3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoic acid

methyl 3-(3-(3-chloro-2-fluorobenzyl)-2,6-difluorophenyl)-3-oxopropanoate

methyl 2-(3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoyl)-3-(dimethylamino)acrylate