4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 1025097-53-3
• Molecular Formula: C₂₄H₂₇FN₂O₇
• Molecular Weight: 474.486
• Mol file: 1025097-53-3.mol

Synonyms:4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidine-1-carboxylic acid benzyl ester

Chemical Property of 4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidine-1-carboxylic acid benzyl ester

There total 5 articles about 4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidine-1-carboxylic acid benzyl ester 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: 94.5%

(R)‐3‐(3‐fluoro‐4‐hydroxyphenyl)‐5‐(hydroxymethyl)oxazolidin‐2‐one (1025097-50-0) + benzyl 1-oxa-6-aza-spiro[2.5]octane-6-carboxylate (77211-75-7) → 4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidine-1-carboxylic acid benzyl ester (1025097-53-3)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; at 100 ℃;

Reference yield:

2-fluoro-4-nitrophenol (403-19-0) → 4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidine-1-carboxylic acid benzyl ester (1025097-53-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium carbonate; potassium iodide / acetone / 60 °C

2.1: iron; ammonium chloride / ethanol; water / 2 h / 90 °C

3.1: sodium hydrogencarbonate / water; tetrahydrofuran / 0.5 h / 0 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 0.5 h

5.1: 5%-palladium/activated carbon; hydrogen / methanol / 12 h / 20 °C / 760.05 Torr

6.1: sodium carbonate / N,N-dimethyl-formamide / 12 h / 100 °C

With n-butyllithium; 5%-palladium/activated carbon; hydrogen; iron; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; ammonium chloride; potassium iodide; In tetrahydrofuran; methanol; ethanol; hexane; water; N,N-dimethyl-formamide; acetone;

DOI:10.3390/molecules24081641

Reference yield:

1-(benzyloxy)-2-fluoro-4-nitrobenzene (76243-24-8) → 4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidine-1-carboxylic acid benzyl ester (1025097-53-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: iron; ammonium chloride / ethanol; water / 2 h / 90 °C

2.1: sodium hydrogencarbonate / water; tetrahydrofuran / 0.5 h / 0 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 0.5 h

4.1: 5%-palladium/activated carbon; hydrogen / methanol / 12 h / 20 °C / 760.05 Torr

5.1: sodium carbonate / N,N-dimethyl-formamide / 12 h / 100 °C

With n-butyllithium; 5%-palladium/activated carbon; hydrogen; iron; sodium hydrogencarbonate; sodium carbonate; ammonium chloride; In tetrahydrofuran; methanol; ethanol; hexane; water; N,N-dimethyl-formamide;

DOI:10.3390/molecules24081641

upstream raw materials:

(R)‐3‐(3‐fluoro‐4‐hydroxyphenyl)‐5‐(hydroxymethyl)oxazolidin‐2‐one

benzyl 1-oxa-6-aza-spiro[2.5]octane-6-carboxylate

2-fluoro-4-nitrophenol

1-(benzyloxy)-2-fluoro-4-nitrobenzene

Downstream raw materials:

(R)-3-[3-fluoro-4-(4-hydroxypiperidin-4-ylmethoxy)phenyl]-5-hydroxymethyloxazolidin-2-one

6-fluoro-7-{4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidin-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

6-fluoro-7-{4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidin-1-yl}-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

1-cyclopropyl-6-fluoro-7-[4-({2-fluoro-4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl] phenoxy}methyl)-4-hydroxypiperidin-1-yl]-4-oxo-1,4-dihydroquinolin-3-carboxylic acid