(5S)-5-Phenyloxazolidin-2-one

Base Information

• Chemical Name: (5S)-5-Phenyloxazolidin-2-one
• CAS No.: 186343-35-1
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.176
• European Community (EC) Number: 867-602-0
• Nikkaji Number: J516.881C
• Wikidata: Q104917335
• Mol file: 186343-35-1.mol

Synonyms:SCHEMBL8809819;(5S)-5-Phenyloxazolidin-2-one;(5S)-5-phenyl-1,3-oxazolidin-2-one;EN300-7902863;186343-35-1

Chemical Property of (5S)-5-Phenyloxazolidin-2-one

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 163.063328530
• Heavy Atom Count: 12
• Complexity: 175

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(=O)N1)C2=CC=CC=C2
• Isomeric SMILES: C1[C@@H](OC(=O)N1)C2=CC=CC=C2

Technology Process of (5S)-5-Phenyloxazolidin-2-one

There total 18 articles about (5S)-5-Phenyloxazolidin-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: 86.0%

(S)-2-Amino-1-phenyl-1-ethanol (56613-81-1,1936-63-6) + 1,1'-carbonyldiimidazole (530-62-1) → (S)-5-phenyl-1,3-oxazolidine-2-one (186343-35-1)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/acs.jmedchem.0c01561

Reference yield: 80.0%

carbon dioxide (124-38-9,18923-20-1) + (S)-2-azido-1-phenylethanol (124817-06-7,18756-01-9) → (S)-5-phenyl-1,3-oxazolidine-2-one (186343-35-1)

Guidance literature:

With triphenylphosphine; In toluene; at 0 - 100 ℃; under 258.581 - 310.297 Torr;

Reference yield: 80.0%

ethyl (R)-3-hydroxy-3-phenylbutanoate (24506-17-0) → (S)-5-phenyl-1,3-oxazolidine-2-one (186343-35-1)

Guidance literature:

With pyridine; lead(IV) acetate;

DOI:10.1016/j.bmcl.2004.11.054

upstream raw materials:

(S)-(+)-N-methoxycarbonyl-2-hydroxy-2-phenylethylamine

(R)-(2-hydroxy-2-phenyl-ethyl)carbamic acid tert-butyl ester

ethyl (R)-3-hydroxy-3-phenylbutanoate

styrene oxide

Downstream raw materials:

(S)-2-Amino-1-phenyl-1-ethanol

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

(4S)-4-phenyl-3-[(2R)-2-phenylpropionyl]oxazolidin-2-one

(S)-(2-hydroxy-2-phenyl-ethyl)carbamic acid tert-butyl ester