N-(trans-2',3',4',5',6'-pentafluorocinnamoyl)oxazolidin-2-one

Base Information

• Chemical Name: N-(trans-2',3',4',5',6'-pentafluorocinnamoyl)oxazolidin-2-one
• CAS No.: 259754-43-3
• Molecular Formula: C₁₂H₆F₅NO₃
• Molecular Weight: 307.177
• Mol file: 259754-43-3.mol

Synonyms:N-(trans-2',3',4',5',6'-pentafluorocinnamoyl)oxazolidin-2-one

Chemical Property of N-(trans-2',3',4',5',6'-pentafluorocinnamoyl)oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(trans-2',3',4',5',6'-pentafluorocinnamoyl)oxazolidin-2-one

There total 2 articles about N-(trans-2',3',4',5',6'-pentafluorocinnamoyl)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: 87.0%

dimethylenecyclourethane (497-25-6) + (E)‐3‐(perfluorophenyl)acryloyl chloride (21514-50-1) → N-(trans-2',3',4',5',6'-pentafluorocinnamoyl)oxazolidin-2-one (259754-43-3)

Guidance literature:

dimethylenecyclourethane; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

(E)‐3‐(perfluorophenyl)acryloyl chloride; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;

DOI:10.1021/jo0008791

Reference yield:

2,3,4,5,6-pentafluoro-trans-cinnamic acid (34234-46-3) → N-(trans-2',3',4',5',6'-pentafluorocinnamoyl)oxazolidin-2-one (259754-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: SOCl₂ / CH₂Cl₂ / 2 h / Heating

2.1: n-BuLi / tetrahydrofuran / -78 °C

2.2: 87 percent / tetrahydrofuran / -78 - 20 °C

With n-butyllithium; thionyl chloride; In tetrahydrofuran; dichloromethane; 1.1: Chlorination / 2.1: deprotonation / 2.2: Acylation;

DOI:10.1021/jo0008791

Reference yield: 73.0%

N-(trans-2',3',4',5',6'-pentafluorocinnamoyl)oxazolidin-2-one (259754-43-3) + Ni(II) complex of the Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]acetophenone → Ni(II) complex of the Schiff base of (S)-o-[N-(N-benzylprolyl)amino]benzophenone and (2R,3S)-3-pentafluorophenyl-5-[3'-(2'-oxazolidinonyl)]glutamic acid + Ni(II) complex of the Schiff base of (S)-o-[N-(N-benzylprolyl)amino]benzophenone and (2S,3R)-3-pentafluorophenyl-5-[3'-(2'-oxazolidinonyl)]glutamic acid

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 ℃; Product distribution;

DOI:10.1021/jo0014865

upstream raw materials:

dimethylenecyclourethane

(E)‐3‐(perfluorophenyl)acryloyl chloride

2,3,4,5,6-pentafluoro-trans-cinnamic acid