(S)-N-((3-(2-fluoro-4'-(hydroxymethyl)-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide

Base Information

• Chemical Name: (S)-N-((3-(2-fluoro-4'-(hydroxymethyl)-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide
• CAS No.: 843647-51-8
• Molecular Formula: C₁₉H₁₉FN₂O₄
• Molecular Weight: 358.369
• Mol file: 843647-51-8.mol

Synonyms:(S)-N-((3-(2-fluoro-4'-(hydroxymethyl)-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide

Chemical Property of (S)-N-((3-(2-fluoro-4'-(hydroxymethyl)-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-((3-(2-fluoro-4'-(hydroxymethyl)-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide

There total 4 articles about (S)-N-((3-(2-fluoro-4'-(hydroxymethyl)-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide 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: 94.0%

p-hydroxymethylphenylboronic acid (59016-93-2) + (S)-N-[3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidine-5-ylmethyl]acetamide (149524-45-8) → (S)-N-((3-(2-fluoro-4'-(hydroxymethyl)-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide (843647-51-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In ethanol; water; toluene; at 25 ℃; for 6h; Heating / reflux;

Reference yield:

(S)-5-(((4-chlorobenzylidene)amino)methyl)-3-(3-fluorophenyl)oxazolidin-2-one → (S)-N-((3-(2-fluoro-4'-(hydroxymethyl)-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide (843647-51-8)

Guidance literature:

Multi-step reaction with 4 steps

1: isobutylamine / toluene / 14 h / 83 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

3: trifluoroacetic acid; N-iodo-succinimide / 2 h / 20 °C / Inert atmosphere

4: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol; water / 10 h / Inert atmosphere; Reflux

With dmap; N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; isobutylamine; potassium carbonate; triethylamine; trifluoroacetic acid; In ethanol; dichloromethane; water; toluene;

DOI:10.1016/j.ejmech.2020.113002

Reference yield:

(S)-5-(aminomethyl)-3-(3-fluorophenyl)oxazolidin-2-one (380380-56-3) → (S)-N-((3-(2-fluoro-4'-(hydroxymethyl)-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide (843647-51-8)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: trifluoroacetic acid; N-iodo-succinimide / 2 h / 20 °C / Inert atmosphere

3: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol; water / 10 h / Inert atmosphere; Reflux

With dmap; N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; triethylamine; trifluoroacetic acid; In ethanol; dichloromethane; water; toluene;

DOI:10.1016/j.ejmech.2020.113002

upstream raw materials:

p-hydroxymethylphenylboronic acid

(S)-N-[3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidine-5-ylmethyl]acetamide

(S)-5-(aminomethyl)-3-(3-fluorophenyl)oxazolidin-2-one

(S)-N-[[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide

Downstream raw materials:

methanesulfonic acid (5S)-4'-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2'-fluoro-biphenyl-4-ylmethyl ester

C₁₉H₁₈ClFN₂O₃