((2'R,4'S)-(+)-3'-Benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl)acetic acid

Base Information

• Chemical Name: ((2'R,4'S)-(+)-3'-Benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl)acetic acid
• CAS No.: 179910-97-5
• Molecular Formula: C₂₅H₂₁NO₅
• Molecular Weight: 415.445
• Mol file: 179910-97-5.mol

Synonyms:((2'R,4'S)-(+)-3'-Benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl)acetic acid

Chemical Property of ((2'R,4'S)-(+)-3'-Benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl)acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2'R,4'S)-(+)-3'-Benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl)acetic acid

There total 3 articles about ((2'R,4'S)-(+)-3'-Benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl)acetic acid 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: 41.0%

(2R,4S)-tert-butyl 3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl ethanoate (258854-42-1) → ((2'R,4'S)-(+)-3'-Benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl)acetic acid (179910-97-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1021/jo991306v

Reference yield:

(2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one (113806-30-7) → ((2'R,4'S)-(+)-3'-Benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl)acetic acid (179910-97-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiHMDS / tetrahydrofuran / 0.12 h / -78 °C

1.2: 87 percent / tetrahydrofuran / -78 - 20 °C

2.1: 41 percent / TFA / CH₂Cl₂ / 0.08 h / 0 °C

With trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1.1: Metallation / 1.2: Alkylation / 2.1: Hydrolysis;

DOI:10.1021/jo991306v

Reference yield:

diphenylmethyl bromoacetate (79287-72-2) + (2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one (113806-30-7) → ((2'R,4'S)-(+)-3'-Benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl)acetic acid (179910-97-5)

Guidance literature:

With trifluoroacetic acid; lithium hexamethyldisilazane; Yield given. Multistep reaction; 1.) THF, -78 deg C, 2 h; -78 deg C to r.t., 16 h, 2.) CH₂Cl₂, 0 deg C, 5 min;

DOI:10.1039/P19960001299

upstream raw materials:

diphenylmethyl bromoacetate

(2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one

(2R,4S)-tert-butyl 3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl ethanoate

Downstream raw materials:

(2R,4S)-ethyl 4-(3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl) 3-oxobutanoate

Ethyl (2'R,4'S)-(+)-4-(3'-benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl)-3-oxo-2-(triphenylphosphoranylidene)butanoate

((2R,4S)-3-Benzoyl-4-benzyl-5-oxo-2-phenyl-oxazolidin-4-yl)-acetyl chloride