(5R)-3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-5-azidomethyl-oxazolidin-2-one

Base Information

• Chemical Name: (5R)-3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-5-azidomethyl-oxazolidin-2-one
• CAS No.: 1207472-12-5
• Molecular Formula: C₁₇H₂₁F₂N₅O₄
• Molecular Weight: 397.382

Synonyms:(5R)-3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-5-azidomethyl-oxazolidin-2-one

Chemical Property of (5R)-3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-5-azidomethyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-5-azidomethyl-oxazolidin-2-one

There total 8 articles about (5R)-3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-5-azidomethyl-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: 93.0%

(5R)-methanesulfonic acid 3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl ester (1207472-07-8) → (5R)-3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-5-azidomethyl-oxazolidin-2-one (1207472-12-5)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 70 ℃; for 8h;

Reference yield:

3,4,5-trifluoronitrobenzene (66684-58-0) → (5R)-3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-5-azidomethyl-oxazolidin-2-one (1207472-12-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine / chloroform / 0.5 h

1.2: 8 h / 65 - 70 °C

2.1: potassium tert-butylate / acetonitrile / 2.5 h / 0 - 5 °C / Inert atmosphere

2.2: 2 h / 5 - 10 °C

3.1: methanol / 26 h / 20 °C

3.2: 1 h

4.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 3 h / 45 - 55 °C / 1551.49 Torr

5.1: sodium hydrogencarbonate / toluene / 2 h / 40 - 45 °C

6.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / 40 °C / Inert atmosphere

6.2: 40 °C

6.3: 0.5 h

7.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 17.25 h / 0 - 20 °C / Inert atmosphere

With n-butyllithium; diphenyl phosphoryl azide; potassium tert-butylate; hydrogen; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium 10% on activated carbon; In tetrahydrofuran; methanol; hexane; chloroform; ethyl acetate; toluene; acetonitrile;

Reference yield:

4-piperidone hydrochloride (41979-39-9) → (5R)-3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-5-azidomethyl-oxazolidin-2-one (1207472-12-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine / chloroform / 0.5 h

1.2: 8 h / 65 - 70 °C

2.1: potassium tert-butylate / acetonitrile / 2.5 h / 0 - 5 °C / Inert atmosphere

2.2: 2 h / 5 - 10 °C

3.1: methanol / 26 h / 20 °C

3.2: 1 h

4.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 3 h / 45 - 55 °C / 1551.49 Torr

5.1: sodium hydrogencarbonate / toluene / 2 h / 40 - 45 °C

6.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / 40 °C / Inert atmosphere

6.2: 40 °C

6.3: 0.5 h

7.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 17.25 h / 0 - 20 °C / Inert atmosphere

With n-butyllithium; diphenyl phosphoryl azide; potassium tert-butylate; hydrogen; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium 10% on activated carbon; In tetrahydrofuran; methanol; hexane; chloroform; ethyl acetate; toluene; acetonitrile;

upstream raw materials:

4-piperidone hydrochloride

3,4,5-trifluoronitrobenzene

1-(2,6-difluoro-4-nitrophenyl)piperidin-4-one

1-(4-amino-2,6-difluoro-phenyl)-4-methoxymethyl-piperidin-4-ol

Downstream raw materials:

(5S)-N-{3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

phosphoric acid mono-(1-{4-[(S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2,6-difluorophenyl}-4-methoxymethyl-piperidin-4-yl) ester

(S)-N-{3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-4-di-O-benzylphosphoryloxy-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

5-aminomethyl-3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-oxazolidin-2-one

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