(4R,5S)-3-((R)-2,3-dimethylbutanoyl)-4-methyl-5-phenyloxazolidin-2-one

Base Information

• Chemical Name: (4R,5S)-3-((R)-2,3-dimethylbutanoyl)-4-methyl-5-phenyloxazolidin-2-one
• CAS No.: 1391831-28-9
• Molecular Formula: C₁₆H₂₁NO₃
• Molecular Weight: 275.348
• Mol file: 1391831-28-9.mol

Synonyms:(4R,5S)-3-((R)-2,3-dimethylbutanoyl)-4-methyl-5-phenyloxazolidin-2-one

Chemical Property of (4R,5S)-3-((R)-2,3-dimethylbutanoyl)-4-methyl-5-phenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-3-((R)-2,3-dimethylbutanoyl)-4-methyl-5-phenyloxazolidin-2-one

There total 4 articles about (4R,5S)-3-((R)-2,3-dimethylbutanoyl)-4-methyl-5-phenyloxazolidin-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: 86.0%

(4R,5S)-(+)-3-[3-methyl-1-oxobut-1-yl]-4-methyl-5-phenyl-2-oxazolidinone (107599-99-5) + methyl iodide (74-88-4) → (4R,5S)-3-((R)-2,3-dimethylbutanoyl)-4-methyl-5-phenyloxazolidin-2-one (1391831-28-9)

Guidance literature:

(4R,5S)-(+)-3-[3-methyl-1-oxobut-1-yl]-4-methyl-5-phenyl-2-oxazolidinone; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 15h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 10h; Inert atmosphere;

DOI:10.1002/anie.201410371

Reference yield: 86.0%

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one (77877-20-4) + methyl iodide (74-88-4) → (4R,5S)-3-((R)-2,3-dimethylbutanoyl)-4-methyl-5-phenyloxazolidin-2-one (1391831-28-9)

Guidance literature:

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one; With sodium hexamethyldisilazane; at -78 ℃; for 15h;

methyl iodide; at -78 ℃; for 10h; optical yield given as %de; diastereoselective reaction;

DOI:10.1002/ejoc.201200147

Reference yield:

4-methyl-5-phenyloxazolidin-2-one (77943-39-6) → (4R,5S)-3-((R)-2,3-dimethylbutanoyl)-4-methyl-5-phenyloxazolidin-2-one (1391831-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane

1.2: 2 h / 20 °C

2.1: sodium hexamethyldisilazane / 15 h / -78 °C

2.2: 10 h / -78 °C

With n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; hexane;

DOI:10.1002/ejoc.201200147

upstream raw materials:

4-methyl-5-phenyloxazolidin-2-one

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

methyl iodide

isopentanoyl chloride

Downstream raw materials:

(R)-2,3-dimethylbutan-1-ol