(S)-2-(benzyloxy)-N-((3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

Base Information

• Chemical Name: (S)-2-(benzyloxy)-N-((3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
• CAS No.: 1293990-10-9
• Molecular Formula: C₂₆H₂₄FN₇O₄
• Molecular Weight: 517.519

Synonyms:(S)-2-(benzyloxy)-N-((3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

Chemical Property of (S)-2-(benzyloxy)-N-((3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

Chemical Property:

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Technology Process of (S)-2-(benzyloxy)-N-((3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

There total 8 articles about (S)-2-(benzyloxy)-N-((3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 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: 75.0%

Benzyloxyacetyl chloride (19810-31-2) + (S)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(aminomethyl)oxazolidin-2-one (1293990-06-3) → (S)-2-(benzyloxy)-N-((3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide (1293990-10-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.ejmech.2011.01.014

Reference yield:

2,5-dibromopyridine (624-28-2) → (S)-2-(benzyloxy)-N-((3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide (1293990-10-9)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium cyanide / N,N-dimethyl-formamide / 7 h / 150 °C / Inert atmosphere

2: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere

3: sodium hydroxide / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

4: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / 1-methyl-pyrrolidin-2-one / 4 h / 120 °C / Inert atmosphere

5: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

6: sodium azide / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere

7: 10% palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C

8: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

With sodium cyanide; bis-triphenylphosphine-palladium(II) chloride; sodium azide; 10% palladium on activated charcoal; hydrogen; ammonium chloride; triethylamine; lithium chloride; sodium hydroxide; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; N,N-dimethyl-formamide; 4: Stille coupling;

DOI:10.1016/j.ejmech.2011.01.014

Reference yield:

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one (856866-72-3) → (S)-2-(benzyloxy)-N-((3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide (1293990-10-9)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2: sodium azide / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere

3: 10% palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C

4: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

With sodium azide; 10% palladium on activated charcoal; hydrogen; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2011.01.014

upstream raw materials:

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

2,5-dibromopyridine

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(methanesulfonyloxymethyl)oxazolidin-2-one

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(azidomethyl)oxazolidin-2-one

Downstream raw materials:

(S)-N-((3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)-2-hydroxyacetamide

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