5-aminomethyl-3-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluoro phenyl]oxazolidin-2-one

Base Information

• Chemical Name: 5-aminomethyl-3-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluoro phenyl]oxazolidin-2-one
• CAS No.: 1403682-01-8
• Molecular Formula: C₁₈H₁₉FN₂O₄
• Molecular Weight: 346.358

Synonyms:5-aminomethyl-3-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluoro phenyl]oxazolidin-2-one

Chemical Property of 5-aminomethyl-3-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluoro phenyl]oxazolidin-2-one

Chemical Property:

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Technology Process of 5-aminomethyl-3-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluoro phenyl]oxazolidin-2-one

There total 8 articles about 5-aminomethyl-3-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluoro phenyl]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: 54.1%

5-aminomethyl-3-[4-(2-benzyloxy-4-ethylphenoxy)-3-fluorophenyl]-oxazolidin-2-one (1419639-38-5) → 5-aminomethyl-3-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluoro phenyl]oxazolidin-2-one (1403682-01-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1021/jm301113w

Reference yield:

3,4-difluoronitrobenzene (369-34-6) → 5-aminomethyl-3-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluoro phenyl]oxazolidin-2-one (1403682-01-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium hydroxide / acetonitrile / 2 h / 80 °C

2.1: tin(ll) chloride; hydrogenchloride / diethyl ether / 0 - 20 °C / Inert atmosphere

3.1: sodium hydrogencarbonate / tetrahydrofuran / 0 - 20 °C

4.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 0 - 20 °C

6.1: sodium azide / N,N-dimethyl-formamide / 75 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C / Inert atmosphere

8.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; sodium azide; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; triethylamine; tin(ll) chloride; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm301113w

Reference yield:

toluene-4-sulfonic acid 4-ethyl-2-methoxy-phenyl ester (952433-90-8) → 5-aminomethyl-3-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluoro phenyl]oxazolidin-2-one (1403682-01-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: boron tribromide / dichloromethane / 6 h / -78 - -20 °C / Inert atmosphere

2.1: potassium carbonate; sodium iodide / acetone / 5 h / 40 °C / Inert atmosphere

3.1: magnesium / methanol / 20 °C / Inert atmosphere

4.1: potassium hydroxide / acetonitrile / 2 h / 80 °C

5.1: tin(ll) chloride; hydrogenchloride / diethyl ether / 0 - 20 °C / Inert atmosphere

6.1: sodium hydrogencarbonate / tetrahydrofuran / 0 - 20 °C

7.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

7.2: -78 - 20 °C / Inert atmosphere

8.1: triethylamine / dichloromethane / 0 - 20 °C

9.1: sodium azide / N,N-dimethyl-formamide / 75 °C / Inert atmosphere

10.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C / Inert atmosphere

11.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; sodium azide; palladium 10% on activated carbon; hydrogen; boron tribromide; sodium hydrogencarbonate; potassium carbonate; magnesium; triethylamine; sodium iodide; tin(ll) chloride; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jm301113w

upstream raw materials:

3,4-difluoronitrobenzene

toluene-4-sulfonic acid 4-ethyl-2-methoxy-phenyl ester

4-ethyl-2-hydroxyphenyl-4-methylbenzenesulfonate

2-benzyloxy-4-ethyl-phenol

Downstream raw materials:

C₂₀H₂₁FN₂O₅

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