2-Oxazolidinone, 3-(1-oxo-2-propenyl)-4-phenyl-, (4S)-

Base Information

• Chemical Name: 2-Oxazolidinone, 3-(1-oxo-2-propenyl)-4-phenyl-, (4S)-
• CAS No.: 259529-54-9
• Molecular Formula: C12H11NO3
• Molecular Weight: 217.224
• DSSTox Substance ID: DTXSID20438922
• Nikkaji Number: J1.272.139K
• Wikidata: Q82254771
• Mol file: 259529-54-9.mol

Synonyms:259529-54-9;2-Oxazolidinone, 3-(1-oxo-2-propenyl)-4-phenyl-, (4S)-;SCHEMBL4956490;DTXSID20438922;3-Acryloyl-4beta-phenyloxazolidine-2-one

Chemical Property of 2-Oxazolidinone, 3-(1-oxo-2-propenyl)-4-phenyl-, (4S)-

Chemical Property:

• PSA: 46.61000
• LogP: 1.83040
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 217.07389321
• Heavy Atom Count: 16
• Complexity: 307

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC(=O)N1C(COC1=O)C2=CC=CC=C2
• Isomeric SMILES: C=CC(=O)N1[C@H](COC1=O)C2=CC=CC=C2

Technology Process of 2-Oxazolidinone, 3-(1-oxo-2-propenyl)-4-phenyl-, (4S)-

There total 8 articles about 2-Oxazolidinone, 3-(1-oxo-2-propenyl)-4-phenyl-, (4S)- 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: 93.0%

(S)-4-phenyl-2-oxazolidinone (99395-88-7,7480-32-2) + acryloyl chloride (814-68-6,25189-84-8) → (4S)-3-(1-oxo-2-propen-1-yl)-4-phenyl-1,3-oxazolidin-2-one (259529-54-9)

Guidance literature:

(S)-4-phenyl-2-oxazolidinone; With chloro-trimethyl-silane; In dichloromethane; at 0 - 10 ℃; for 0.5h;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 10 ℃; for 2h;

acryloyl chloride; With tetrabutyl ammonium fluoride; In dichloromethane; at 0 - 20 ℃; for 2h; Reagent/catalyst;

Reference yield: 81.0%

(S)-4-phenyl-2-oxazolidinone (99395-88-7,7480-32-2) + acrylic acid (79-10-7) → (4S)-3-(1-oxo-2-propen-1-yl)-4-phenyl-1,3-oxazolidin-2-one (259529-54-9)

Guidance literature:

acrylic acid; With N-ethyl-N,N-diisopropylamine; acryloyl chloride; In tetrahydrofuran; at 25 ℃; for 1h;

(S)-4-phenyl-2-oxazolidinone; With lithium chloride; In tetrahydrofuran; for 1h;

DOI:10.1021/acs.joc.0c02639

Reference yield: 79.0%

acrylic acid (79-10-7) + lithium (S)-2-oxo-4-phenyloxazolidin-3-ide → (4S)-3-(1-oxo-2-propen-1-yl)-4-phenyl-1,3-oxazolidin-2-one (259529-54-9)

Guidance literature:

acrylic acid; With 4-methyl-morpholine; pivaloyl chloride; In tetrahydrofuran; at -78 ℃; for 1h;

lithium (S)-2-oxo-4-phenyloxazolidin-3-ide; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;

DOI:10.1021/ol0157609

upstream raw materials:

acrylic acid

acrylic acid anhydride

(S)-4-phenyl-2-oxazolidinone

acryloyl chloride

Downstream raw materials:

(2'S,2R,3S)-{[3,4-dihydro-2-(4-nitrophenyl)-5-phenyl-2H-pyrrol-3-yl]-carbonyl}-2-oxo-4-phenyloxazolidine

(S)-3-((2S,3S)-3-(3,5-di-tert-butylphenyl)-2-((dimethyl(phenyl)silyl)methyl)-3-hydroxy-propanoyl)-4-phenyloxazolidin-2-one

(S)-3-((2S,3S)-2-((dimethyl(phenyl)silyl)methyl)-3-(4-fluorophenyl)-3-hydroxypropanoyl)-4-phenyloxazolidin-2-one

(S)-3-((2S,3S)-2-((dimethyl(phenyl)silyl)methyl)-3-hydroxy-phenylpropanoyl)-4-phenyloxazolidin-2-one

Refernces

• 1、 -. "Preparation method of ezetimibe intermediate". Paragraph 0052; 0053; 0054; 0055. . Retrieved 2016/11/14.
• 2、 Li, Lei,Hu, Weimin,Jia, Yanxing. "Synthetic studies of cyclic peptides stephanotic acid methyl ester, celogentin C, and moroidin". . p. 7753 - 7762. Retrieved 2014/12/10.