(S)-N-[[3-[3-Fluoro-4-[4-(hydroxymethyl)-1H-imidazol-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Base Information

Chemical Name:(S)-N-[[3-[3-Fluoro-4-[4-(hydroxymethyl)-1H-imidazol-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
CAS No.:196299-14-6
Molecular Formula:C₁₆H₁₇FN₄O₄
Molecular Weight:348.334
Hs Code.:

Synonyms:(S)-N-[[3-[3-Fluoro-4-[4-(hydroxymethyl)-1H-imidazol-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

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Chemical Property of (S)-N-[[3-[3-Fluoro-4-[4-(hydroxymethyl)-1H-imidazol-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

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Technology Process of (S)-N-[[3-[3-Fluoro-4-[4-(hydroxymethyl)-1H-imidazol-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

There total 11 articles about (S)-N-[[3-[3-Fluoro-4-[4-(hydroxymethyl)-1H-imidazol-1-yl]phenyl]-2-oxo-5-oxazolidinyl]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: 96.0%

: 196299-12-4
N-[((5S)-3-{4-[4-({[tert-butyldimethylsilyl]oxy}methyl)-1H-imidazol-1-yl]-3-fluorophenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide

: 196299-14-6
(S)-N-[[3-[3-Fluoro-4-[4-(hydroxymethyl)-1H-imidazol-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

Reference yield:

: 196299-10-2
5-azidomethyl-3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-yl]-3-fluoro-phenyl}-oxazolidin-2-one

: 196299-14-6
(S)-N-[[3-[3-Fluoro-4-[4-(hydroxymethyl)-1H-imidazol-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Guidance literature:: Multi-step reaction with 3 steps

1: H₂ / Pd/C / methanol; tetrahydrofuran / 24 h / 760.05 Torr

2: pyridine / CH₂Cl₂ / 20 °C

3: 1.27 g / AcOH; THF / H₂O / 16 h / 20 °C

With tetrahydrofuran; pyridine; hydrogen; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; 1: Reduction / 2: Acetylation / 3: desilylation;
DOI:10.1021/jm990373e

Reference yield:

: 369-34-6
3,4-difluoronitrobenzene

: 196299-14-6
(S)-N-[[3-[3-Fluoro-4-[4-(hydroxymethyl)-1H-imidazol-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: 47 percent / K₂CO₃ / acetone / 24 h / Heating

2.1: 64 percent / imidazole / dimethylformamide / 0 - 20 °C

3.1: H₂ / tetrahydrofuran / 18 h

4.1: NaHCO₃ / tetrahydrofuran / 0 - 20 °C

5.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -78 °C

5.2: tetrahydrofuran / -78 - 20 °C

6.1: NEt₃ / CH₂Cl₂ / 4 h / 20 °C

7.1: NaN₃ / dimethylformamide / 65 °C

8.1: H₂ / Pd/C / methanol; tetrahydrofuran / 24 h / 760.05 Torr

9.1: pyridine / CH₂Cl₂ / 20 °C

10.1: 1.27 g / AcOH; THF / H₂O / 16 h / 20 °C

With tetrahydrofuran; pyridine; 1H-imidazole; sodium azide; hydrogen; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1.1: Substitution / 2.1: silylation / 3.1: Reduction / 4.1: Acylation / 5.1: Metallation / 5.2: Ring cleavage / 6.1: mesylation / 7.1: Substitution / 8.1: Reduction / 9.1: Acetylation / 10.1: desilylation;
DOI:10.1021/jm990373e