(4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

Base Information

• Chemical Name: (4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
• CAS No.: 108656-28-6
• Molecular Formula: C₁₁H₁₂FNO₄S
• Molecular Weight: 273.285
• Mol file: 108656-28-6.mol

Synonyms:(4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

Chemical Property of (4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

There total 20 articles about (4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone 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: 81.0%

(4R,5R)-4-hydroxymethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone (96795-22-1) → (4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone (108656-28-6)

Guidance literature:

With DAST; In tetrahydrofuran; at -60 - 20 ℃; for 21h; Inert atmosphere;

DOI:10.1021/acs.joc.0c02181

Reference yield:

para-methanesulfonylbenzaldehyde (5398-77-6) → (4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone (108656-28-6)

Guidance literature:

Multi-step reaction with 5 steps

1: C₂₉H₂₈F₆N₄O₂ / chloroform / 60 h / -60 °C

2: potassium hydroxide / water; tetrahydrofuran / 0.17 h / 0 °C / 7500.75 Torr

3: 1H-imidazole / tetrahydrofuran / 0.13 h / 70 °C / 7500.75 Torr

4: sodium tetrahydroborate / methanol / 4.33 h / 20 °C

5: DAST / tetrahydrofuran / 21 h / -60 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; C₂₉H₂₈F₆N₄O₂; potassium hydroxide; In tetrahydrofuran; methanol; chloroform; water;

DOI:10.1021/acs.joc.0c02181

Reference yield:

4-((4S,5R)-4-(fluoromethyl)-2-oxooxazolidin-5-yl)benzene-1-sulfonyl chloride (1470142-34-7) + methyl iodide (74-88-4) → (4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone (108656-28-6)

Guidance literature:

4-((4S,5R)-4-(fluoromethyl)-2-oxooxazolidin-5-yl)benzene-1-sulfonyl chloride; With sodium hydrogencarbonate; sodium sulfite; In water; at 70 ℃;

methyl iodide; In tetrahydrofuran; water; at -45 - 40 ℃; for 6h; Sealed tube; Inert atmosphere;

DOI:10.1002/jlcr.3053

upstream raw materials:

(4R,5R)-4-hydroxymethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

(R*,R*)-(+)-thiomicamine

(1R,2R)-2-amino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol

(4R,5R)-4-hydroxymethyl-5-<4-(methylthio)phenyl>-2-oxazolidinone

Downstream raw materials:

thiamphenicol

Florfenicol

(1R,2S)-2-(2,3-dimethylbenzoyl)amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol

(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol