Benzoic acid (2R,4S)-4-azido-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-5-oxo-pentyl ester

Base Information

• Chemical Name: Benzoic acid (2R,4S)-4-azido-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-5-oxo-pentyl ester
• CAS No.: 753487-50-2
• Molecular Formula: C₂₃H₂₄N₄O₅
• Molecular Weight: 436.467
• Mol file: 753487-50-2.mol

Synonyms:Benzoic acid (2R,4S)-4-azido-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-5-oxo-pentyl ester

Chemical Property of Benzoic acid (2R,4S)-4-azido-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-5-oxo-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,4S)-4-azido-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-5-oxo-pentyl ester

There total 4 articles about Benzoic acid (2R,4S)-4-azido-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-5-oxo-pentyl ester 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: 73.0%

Benzoic acid (R)-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-5-oxo-pentyl ester (753487-49-9) → Benzoic acid (2R,4S)-4-azido-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-5-oxo-pentyl ester (753487-50-2)

Guidance literature:

Benzoic acid (R)-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-5-oxo-pentyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

With 2,4,6-Triisopropylbenzenesulfonyl azide; In tetrahydrofuran; at -78 ℃; for 0.05h;

With potassium acetate; acetic acid; In tetrahydrofuran; at 30 ℃; for 2.5h;

DOI:10.1021/ol049065n

Reference yield:

Benzoic acid (R)-4-carboxy-2-methyl-butyl ester (914641-62-6) → Benzoic acid (2R,4S)-4-azido-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-5-oxo-pentyl ester (753487-50-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (COCl)2; DMF / CH₂Cl₂ / 2 h / 20 °C

2.1: 7.21 g / tetrahydrofuran / 4 h / -78 - 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: trisyl azide / tetrahydrofuran / 0.05 h / -78 °C

3.3: 73 percent / KOAc; HOAc / tetrahydrofuran / 2.5 h / 30 °C

With oxalyl dichloride; sodium hexamethyldisilazane; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol049065n

Reference yield:

Benzoic acid (R)-4-chlorocarbonyl-2-methyl-butyl ester → Benzoic acid (2R,4S)-4-azido-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-5-oxo-pentyl ester (753487-50-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 7.21 g / tetrahydrofuran / 4 h / -78 - 20 °C

2.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: trisyl azide / tetrahydrofuran / 0.05 h / -78 °C

2.3: 73 percent / KOAc; HOAc / tetrahydrofuran / 2.5 h / 30 °C

With sodium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/ol049065n

upstream raw materials:

Benzoic acid (R)-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-5-oxo-pentyl ester

Benzoic acid (R)-4-carboxy-2-methyl-butyl ester

(4R)-5-benzoyloxy-4-methyl-pentanoic acid tert-butyl ester

Downstream raw materials:

Benzoic acid (2R,4S)-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-4-tert-butoxycarbonylamino-2-methyl-5-oxo-pentyl ester

Benzoic acid (2R,4S)-4-tert-butoxycarbonylamino-4-carboxy-2-methyl-butyl ester