(-)-(5S)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-2'-methoxy-5'-(propan-2-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4,4-dimethyl-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (-)-(5S)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-2'-methoxy-5'-(propan-2-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4,4-dimethyl-1,3-oxazolidin-2-one
• CAS No.: 1312671-81-0
• Molecular Formula: C₃₁H₂₇F₁₀NO₃
• Molecular Weight: 651.544
• Mol file: 1312671-81-0.mol

Synonyms:

Chemical Property of (-)-(5S)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-2'-methoxy-5'-(propan-2-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4,4-dimethyl-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(5S)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-2'-methoxy-5'-(propan-2-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4,4-dimethyl-1,3-oxazolidin-2-one

There total 18 articles about (-)-(5S)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-2'-methoxy-5'-(propan-2-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4,4-dimethyl-1,3-oxazolidin-2-one 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-(2-fluoro-4-methoxyphenyl)-1-ethanone (74457-86-6) → (+)-(5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-2'-methoxy-5'-(propan-2-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4,4-dimethyl-1,3-oxazolidin-2-one (875549-49-8) + (-)-(5S)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-2'-methoxy-5'-(propan-2-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4,4-dimethyl-1,3-oxazolidin-2-one (1312671-81-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0 - 25 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 25 °C / 760.05 Torr

4.1: iodine; silver sulfate / methanol / 3 h / 25 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

5.2: 3 h / -78 °C / Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; water; benzene / 24 h / Inert atmosphere; Reflux

7.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 25 °C / Inert atmosphere

8.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 25 °C / Inert atmosphere

8.2: 15 h / 25 °C / Inert atmosphere

9.1: chiral HPLC, IA column / Resolution of racemate

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; carbon tetrabromide; palladium 10% on activated carbon; hydrogen; iodine; sodium hydride; sodium carbonate; silver sulfate; methanesulfonyl chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm200484c

Reference yield:

benzyl 1-(methoxy(methyl)amino)-2-methyl-1-oxopropan-2-ylcarbamate (875549-00-1) → (+)-(5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-2'-methoxy-5'-(propan-2-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4,4-dimethyl-1,3-oxazolidin-2-one (875549-49-8) + (-)-(5S)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-2'-methoxy-5'-(propan-2-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4,4-dimethyl-1,3-oxazolidin-2-one (1312671-81-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 4 h / -78 °C / Inert atmosphere

2.1: tetrahydrofuran / 3 h / -20 - 25 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 25 °C / Inert atmosphere

3.2: 15 h / 25 °C / Inert atmosphere

4.1: chiral HPLC, IA column / Resolution of racemate

With sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm200484c

Reference yield:

[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]boronic acid (875446-29-0) → (+)-(5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-2'-methoxy-5'-(propan-2-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4,4-dimethyl-1,3-oxazolidin-2-one (875549-49-8) + (-)-(5S)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-2'-methoxy-5'-(propan-2-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4,4-dimethyl-1,3-oxazolidin-2-one (1312671-81-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; water; benzene / 24 h / Inert atmosphere; Reflux

2.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 25 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 25 °C / Inert atmosphere

3.2: 15 h / 25 °C / Inert atmosphere

4.1: chiral HPLC, IA column / Resolution of racemate

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; sodium hydride; sodium carbonate; triphenylphosphine; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm200484c

upstream raw materials:

benzyl 1-(methoxy(methyl)amino)-2-methyl-1-oxopropan-2-ylcarbamate

[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]boronic acid

(4'-fluoro-5'-isopropyl-2'-methoxy-4-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)methanol

2-iodo-5-(trifluoromethyl)benzonitrile

Refernces