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

Base Information

• Chemical Name: (2R,4S)-tert-butyl 3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl ethanoate
• CAS No.: 258854-42-1
• Molecular Formula: C₂₉H₂₉NO₅
• Molecular Weight: 471.553
• Mol file: 258854-42-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

bromoacetic acid tert-butyl ester (5292-43-3) + (2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one (113806-30-7) → (2R,4S)-tert-butyl 3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl ethanoate (258854-42-1)

Guidance literature:

(2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.116667h;

bromoacetic acid tert-butyl ester; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/jo991306v

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)-tert-butyl 3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl ethanoate (258854-42-1) → (3S,E)-3-benzoylamino-3-benzyl-5-ethoxycarbonylmethylidene-1-methyl-2-pyrrolidinone

Guidance literature:

Multi-step reaction with 4 steps

1.1: 41 percent / TFA / CH₂Cl₂ / 0.08 h / 0 °C

2.1: oxalyl chloride; dimethylformamide / CH₂Cl₂ / 0 - 20 °C

3.1: pyridine / CH₂Cl₂ / 0 - 20 °C

3.2: 203 mg / 2.5 h / Heating

4.1: 1,2-dichloro-ethane / 1.5 h / Heating

4.2: 43 percent / 1 h / 150 °C / 1 Torr

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; trifluoroacetic acid; In dichloromethane; 1,2-dichloro-ethane; 1.1: Hydrolysis / 2.1: Chlorination / 3.1: Substitution / 3.2: Ring cleavage / 4.1: Condensation / 4.2: Cyclization;

DOI:10.1021/jo991306v

upstream raw materials:

bromoacetic acid tert-butyl ester

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

Downstream raw materials:

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

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

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