3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-yImethyl methanesulfonate

Base Information

• Chemical Name: 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-yImethyl methanesulfonate
• CAS No.: 1087353-64-7
• Molecular Formula: C₂₁H₂₉FN₂O₇SSi
• Molecular Weight: 500.62
• Mol file: 1087353-64-7.mol

Synonyms:3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-yImethyl methanesulfonate

Chemical Property of 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-yImethyl methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-yImethyl methanesulfonate

There total 11 articles about 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-yImethyl methanesulfonate 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: 98.0%

3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-5-(R)-hydroxymethyl-oxazolidin-2-one (1087353-62-5) + methanesulfonyl chloride (124-63-0) → 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-yImethyl methanesulfonate (1087353-64-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 ℃; for 0.166667h;

Reference yield:

2-fluoro-4-nitrotoluene (1427-07-2) → 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-yImethyl methanesulfonate (1087353-64-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: chromium(VI) oxide; sulfuric acid; acetic acid / water / 3 h / 100 °C

2.1: triethylamine / dmap / dichloromethane / 2 h / 10 - 20 °C

3.1: iron; ammonium chloride / ethanol; water / 1 h / 95 °C

4.1: sodium hydrogencarbonate / tetrahydrofuran / 19 h / 0 - 50 °C

5.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C

6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C

7.1: Burgess Reagent / tetrahydrofuran / 3 h / 75 °C

8.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 0 °C

8.2: 0.5 h / 0 °C

9.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C

10.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

10.2: -78 - 20 °C

11.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.17 h / 0 °C

With 1H-imidazole; chromium(VI) oxide; lithium aluminium tetrahydride; n-butyllithium; Burgess Reagent; sulfuric acid; iron; sodium hydrogencarbonate; ammonium chloride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; dmap; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

2-fluoro-4-nitrobenzoic acid (403-24-7) → 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-yImethyl methanesulfonate (1087353-64-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triethylamine / dmap / dichloromethane / 2 h / 10 - 20 °C

2.1: iron; ammonium chloride / ethanol; water / 1 h / 95 °C

3.1: sodium hydrogencarbonate / tetrahydrofuran / 19 h / 0 - 50 °C

4.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C

6.1: Burgess Reagent / tetrahydrofuran / 3 h / 75 °C

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 0 °C

7.2: 0.5 h / 0 °C

8.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C

9.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

9.2: -78 - 20 °C

10.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.17 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; Burgess Reagent; iron; sodium hydrogencarbonate; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; dmap; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-5-(R)-hydroxymethyl-oxazolidin-2-one

methanesulfonyl chloride

4-(((benzyloxy)carbonyl)amino)-2-fluorobenzoic acid

benzyl [3-fluoro-4-(4-hydroxymethyl-oxazol-2-yl)-phenyl]-carbamate

Downstream raw materials:

5-(R)-azidomethyl-3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-oxazolidin-2-one

5-(R)-azidomethyl-3-[4-(4-chloromethyl-oxazol-2-yl)-3-fluoro-phenyl]-oxazolidin-2-one

5-(R)-azidomethyl-3-[3-fluoro-4-(4-hydroxymethyl-oxazol-2-yl)-phenyl]-oxazolidin-2-one

C₁₇H₁₆FN₅O₃

Refernces