(4R)-3-{(2S)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propionyl}-4-benzyl-2-oxazolidinone

Base Information

• Chemical Name: (4R)-3-{(2S)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propionyl}-4-benzyl-2-oxazolidinone
• CAS No.: 225227-07-6
• Molecular Formula: C₂₅H₂₈N₂O₅
• Molecular Weight: 436.508
• Mol file: 225227-07-6.mol

Synonyms:(4R)-3-{(2S)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propionyl}-4-benzyl-2-oxazolidinone

Chemical Property of (4R)-3-{(2S)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propionyl}-4-benzyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-3-{(2S)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propionyl}-4-benzyl-2-oxazolidinone

There total 2 articles about (4R)-3-{(2S)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propionyl}-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: 87.0%

benzyl chloroformate (501-53-1,94274-21-2) + (4R)-3-[(2S)-2-{[(2S)-1-benzoyloxypyrrolidin-2-yl]propionyl}]-4-benzyl-2-oxazolidinone (321851-45-0) → (4R)-3-{(2S)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propionyl}-4-benzyl-2-oxazolidinone (225227-07-6)

Guidance literature:

(4R)-3-[(2S)-2-{[(2S)-1-benzoyloxypyrrolidin-2-yl]propionyl}]-4-benzyl-2-oxazolidinone; With hydrogen; palladium on activated charcoal; In methanol; acetic acid; at 20 ℃; for 12h;

benzyl chloroformate; With potassium carbonate; In tetrahydrofuran; water; at 20 ℃; for 1.5h;

DOI:10.1246/bcsj.73.2423

Reference yield:

(3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) + (2RS)-1-[(enzyloxy)carbonyl]-2-ethoxypyrrolidine (106412-39-9) → (4R)-3-{(2S)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propionyl}-4-benzyl-2-oxazolidinone (225227-07-6) + (R)-2-[(S)-2-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-1-methyl-2-oxo-ethyl]-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -23 ℃; for 0.75h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(99)00398-6

Reference yield:

(4R)-3-{(2S)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propionyl}-4-benzyl-2-oxazolidinone (225227-07-6) → (S)-2-((S)-1-Carboxy-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water;

DOI:10.1246/bcsj.73.2423

upstream raw materials:

(3R)-3-propionyl-4-benzyloxazolidin-2-one

(2RS)-1-[(enzyloxy)carbonyl]-2-ethoxypyrrolidine

benzyl chloroformate

(4R)-3-[(2S)-2-{[(2S)-1-benzoyloxypyrrolidin-2-yl]propionyl}]-4-benzyl-2-oxazolidinone