(S)-3-[(3S,4R)-1-Benzyl-2-oxo-4-((E)-styryl)-azetidin-3-yl]-4-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: (S)-3-[(3S,4R)-1-Benzyl-2-oxo-4-((E)-styryl)-azetidin-3-yl]-4-phenyl-oxazolidin-2-one
• CAS No.: 99333-60-5
• Molecular Formula: C₂₇H₂₄N₂O₃
• Molecular Weight: 424.499
• Mol file: 99333-60-5.mol

Synonyms:(S)-3-[(3S,4R)-1-Benzyl-2-oxo-4-((E)-styryl)-azetidin-3-yl]-4-phenyl-oxazolidin-2-one

Chemical Property of (S)-3-[(3S,4R)-1-Benzyl-2-oxo-4-((E)-styryl)-azetidin-3-yl]-4-phenyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(3S,4R)-1-Benzyl-2-oxo-4-((E)-styryl)-azetidin-3-yl]-4-phenyl-oxazolidin-2-one

There total 15 articles about (S)-3-[(3S,4R)-1-Benzyl-2-oxo-4-((E)-styryl)-azetidin-3-yl]-4-phenyl-oxazolidin-2-one 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:

carbon monoxide (201230-82-2) + N-(3-phenylprop-2-enylidene)benzylamine (99333-56-9) → (S)-3-[(3S,4S)-1-Benzyl-2-oxo-4-((E)-styryl)-azetidin-3-yl]-4-phenyl-oxazolidin-2-one (134679-71-3) + (S)-3-[(3S,4R)-1-Benzyl-2-oxo-4-((E)-styryl)-azetidin-3-yl]-4-phenyl-oxazolidin-2-one (99333-60-5) + (S)-3-[(3R,4S)-1-Benzyl-2-oxo-4-((E)-styryl)-azetidin-3-yl]-4-phenyl-oxazolidin-2-one (134679-67-7)

Guidance literature:

In dichloromethane; for 0.5h; under 4137.2 Torr; Yield given. Yields of byproduct given; Ambient temperature; Irradiation;

DOI:10.1021/ja00015a036

Reference yield:

2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride (99333-55-8) + N-(3-phenylprop-2-enylidene)benzylamine (99333-56-9) → (S)-3-[(3S,4R)-1-Benzyl-2-oxo-4-((E)-styryl)-azetidin-3-yl]-4-phenyl-oxazolidin-2-one (99333-60-5)

Guidance literature:

With triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, toluene, 0 deg C, 2 h;

DOI:10.1021/ja00015a036

Reference yield:

2-[(R)-2-oxo-4-phenyloxazolidin-3-yl]acetic acid (123882-32-6) → (4R,3'S,4'S)-3-<2'-oxo-4'-(2-phenylethenyl)-1'-(phenylmethyl)-3'-azetidinyl>-4-phenyl-2-oxazolidinone (99333-60-5,129829-29-4,134679-67-7,134679-71-3,135821-29-3)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / toluene / 3 h / 60 °C

2: 1) Et₃N / 1) CH₂Cl₂, -78 deg C, 15 min, 2) toluene, 0 deg C, 3 h

With oxalyl dichloride; triethylamine; In toluene;

DOI:10.1021/jo00018a035

upstream raw materials:

2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride

N-(3-phenylprop-2-enylidene)benzylamine

2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid

ethyl 2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetate

Downstream raw materials:

cis-(3R,4R)-1-benzyl-4-formyl-3-<(4R)-2-oxo-4-phenyloxazolidin-3-yl>azetidin-2-one

(4R,3'R,4'R)-3-<4'-(hydroxymethyl)-2'-oxo-1'-(phenylmethyl)-3'-azetidinyl>-4-phenyl-2-oxazolidinone