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

Base Information

• Chemical Name: 5-(R)-azidomethyl-3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-oxazolidin-2-one
• CAS No.: 1087353-65-8
• Molecular Formula: C₂₀H₂₆FN₅O₄Si
• Molecular Weight: 447.541
• Mol file: 1087353-65-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about 5-(R)-azidomethyl-3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-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: 85.0%

3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-yImethyl methanesulfonate (1087353-64-7) → 5-(R)-azidomethyl-3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-oxazolidin-2-one (1087353-65-8)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 75 ℃; for 2h;

Reference yield:

2-fluoro-4-nitrotoluene (1427-07-2) → 5-(R)-azidomethyl-3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-oxazolidin-2-one (1087353-65-8)

Guidance literature:

Multi-step reaction with 12 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

12.1: sodium azide / N,N-dimethyl-formamide / 2 h / 75 °C

With 1H-imidazole; chromium(VI) oxide; lithium aluminium tetrahydride; n-butyllithium; sodium azide; 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) → 5-(R)-azidomethyl-3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-oxazolidin-2-one (1087353-65-8)

Guidance literature:

Multi-step reaction with 11 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

11.1: sodium azide / N,N-dimethyl-formamide / 2 h / 75 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; sodium azide; 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}-2-oxo-oxazolidin-5-yImethyl methanesulfonate

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

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

methyl 2-(4-benzyloxycarbonylamino-2-fluoro-phenyl)-4,5-oxazole-4-carboxylate

Downstream raw materials:

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

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

C₁₇H₁₆FN₅O₃

5-(R)-azidomethyl-3-[3-fluoro-4-(4-[1,2,4]triazol-1-ylmethyl-oxazol-2-yl)-phenyl]-oxazolidin-2-one

Refernces