(S)-4-benzyl-3-((R)-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-benzyl-3-((R)-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one
• CAS No.: 1414348-90-5
• Molecular Formula: C₁₅H₁₆F₃NO₃
• Molecular Weight: 315.292
• Mol file: 1414348-90-5.mol

Synonyms:(S)-4-benzyl-3-((R)-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one

Chemical Property of (S)-4-benzyl-3-((R)-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-benzyl-3-((R)-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one

There total 2 articles about (S)-4-benzyl-3-((R)-4,4,4-trifluoro-3-methylbutanoyl)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: 57.0%

iodotrifluoromethane (2314-97-8,263005-66-9) + (4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone (90719-30-5) → (S)-4-benzyl-3-((S)-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one (952714-68-0) + (S)-4-benzyl-3-((R)-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one (1414348-90-5) + (S)-4-benzyl-3-butyryloxazolidin-2-one (111292-87-6,143097-11-4,112459-79-7)

Guidance literature:

(4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone; With magnesium(II) perchlorate; In dichloromethane; at 20 ℃;

iodotrifluoromethane; With triethyl borane; oxygen; tri-n-butyl-tin hydride; In hexane; dichloromethane; at -40 ℃; Schlenk technique;

DOI:10.1039/c2ob26810h

Reference yield:

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (S)-4-benzyl-3-((R)-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one (1414348-90-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 2 h / -78 °C

2.1: ytterbium(III) trifluoromethanesulfonate hydrate / tetrahydrofuran; dichloromethane / 0.5 h / 20 °C

2.2: -78 °C / Schlenk technique

With n-butyllithium; ytterbium(III) trifluoromethanesulfonate hydrate; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1039/c2ob26810h

Reference yield: 48.0%

(S)-4-benzyl-3-((R)-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one (1414348-90-5) → (S)-3-((2R,3R)-2-azido-4,4,4-trifluoro-3-methylbutanoyl)-4-benzyloxazolidin-2-one (1414349-00-0) + (S)-3-((2S,3R)-2-azido-4,4,4-trifluoro-3-methylbutanoyl)-4-benzyloxazolidin-2-one (1414349-15-7)

Guidance literature:

(S)-4-benzyl-3-((R)-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

With 2,4,6-Triisopropylbenzenesulfonyl azide; In tetrahydrofuran; toluene; at -78 ℃; for 0.133333h;

With acetic acid; In tetrahydrofuran; toluene; at -78 - 20 ℃; diastereoselective reaction;

DOI:10.1039/c2ob26810h

upstream raw materials:

iodotrifluoromethane

(4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone

(S)-4-Benzyl-2-oxazolidinone

Downstream raw materials:

(S)-3-((2R,3R)-2-azido-4,4,4-trifluoro-3-methylbutanoyl)-4-benzyloxazolidin-2-one

(S)-3-((2S,3R)-2-azido-4,4,4-trifluoro-3-methylbutanoyl)-4-benzyloxazolidin-2-one

tert-butyl ((2S,3R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4,4,4-trifluoro-3-methyl-1-oxobutan-2-yl)carbamate

tert-butyl ((2R,3R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4,4,4-trifluoro-3-methyl-1-oxobutan-2-yl)carbamate