(3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-2-oxazolidinone

Base Information

• Chemical Name: (3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-2-oxazolidinone
• CAS No.: 868248-77-5
• Molecular Formula: C₁₆H₂₀N₄O₃
• Molecular Weight: 316.36
• Mol file: 868248-77-5.mol

Synonyms:(3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-2-oxazolidinone

Chemical Property of (3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-2-oxazolidinone

There total 6 articles about (3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-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: 91.0%

(4S)-3-(5-azido-1-oxovaleryl)-4-benzyl-2-oxazolidinone (868248-75-3) + methyl iodide (74-88-4) → (3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-2-oxazolidinone (868248-77-5)

Guidance literature:

(4S)-3-(5-azido-1-oxovaleryl)-4-benzyl-2-oxazolidinone; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

methyl iodide; In tetrahydrofuran; toluene; at -78 - 0 ℃; for 3h;

DOI:10.1016/j.tetlet.2005.08.056

Reference yield:

(4S)-3-(5-azido-1-oxovaleryl)-4-benzyl-2-oxazolidinone (868248-75-3) + methyl iodide (74-88-4) → (3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-2-oxazolidinone (868248-77-5) + C16H20N4O3

Guidance literature:

1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-5-azido-1-pentanone; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

methyl iodide; In tetrahydrofuran; toluene; at -78 - 0 ℃; for 2h;

DOI:10.1021/acs.jmedchem.0c02036

Reference yield:

5-bromopentanoic acid (2067-33-6) → (3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-2-oxazolidinone (868248-77-5) + C16H20N4O3

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium azide / dimethyl sulfoxide

2.1: pivaloyl chloride; triethylamine / tetrahydrofuran / 1 h / -78 - 0 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C

3.2: 2 h / -78 - 0 °C

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C

4.2: 2 h / -78 - 0 °C

With n-butyllithium; sodium azide; pivaloyl chloride; potassium hexamethylsilazane; triethylamine; In tetrahydrofuran; hexane; dimethyl sulfoxide; toluene;

DOI:10.1021/acs.jmedchem.0c02036

upstream raw materials:

(4S)-3-(5-azido-1-oxovaleryl)-4-benzyl-2-oxazolidinone

methyl iodide

5-azidovaleric acid

5-bromopentanoic acid