(S)-4-Phenyl-3-propionyloxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Phenyl-3-propionyloxazolidin-2-one
• CAS No.: 184363-66-4
• Molecular Formula: C12H13NO3
• Molecular Weight: 219.24
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID70373071
• Nikkaji Number: J788.152E
• Mol file: 184363-66-4.mol

Synonyms:184363-66-4;(S)-4-Phenyl-3-propionyloxazolidin-2-one;(S)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE;(4S)-4-phenyl-3-propanoyl-1,3-oxazolidin-2-one;SCHEMBL6958262;DTXSID70373071;MFCD06658224;AKOS004909708;3-Propionyl-4beta-phenyloxazolidin-2-one;DS-18244;CS-0093681;F16824

Chemical Property of (S)-4-Phenyl-3-propionyloxazolidin-2-one

Chemical Property:

• Vapor Pressure: 2.18E-06mmHg at 25°C
• Refractive Index: 1.553
• Boiling Point: 393.1 °C at 760 mmHg
• Flash Point: 191.6 °C
• PSA: 46.61000
• Density: 1.223 g/cm³
• LogP: 2.05440
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 219.08954328
• Heavy Atom Count: 16
• Complexity: 284

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-4-Phenyl-3-propionyloxazolidin-2-one 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-4-Phenyl-3-propionyloxazolidin-2-one

There total 5 articles about (S)-4-Phenyl-3-propionyloxazolidin-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: 91.3%

(S)-4-phenyl-2-oxazolidinone (99395-88-7,7480-32-2) + propionic acid (802294-64-0,79-09-4) → (4S)-4-benzyl-3-propionyl-1,3-oxazolidin-2-one (184363-66-4)

Guidance literature:

With 2-chloro-1-methylpyridinium p-toluenesulfonate; triethylamine; In dichloromethane; at 25 ℃; for 5h;

Reference yield: 82.0%

propionyl chloride (79-03-8) + (S)-4-phenyl-2-oxazolidinone (99395-88-7,7480-32-2) → (4S)-4-benzyl-3-propionyl-1,3-oxazolidin-2-one (184363-66-4)

Guidance literature:

With triethylamine; In toluene; at 25 - 50 ℃; for 1h;

DOI:10.1021/op0501085

Reference yield: 65.0%

(S)-4-phenyl-2-oxazolidinone (99395-88-7,7480-32-2) + C8H14O3 (220170-24-1) → (4S)-4-benzyl-3-propionyl-1,3-oxazolidin-2-one (184363-66-4)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1055/s-1996-4402

upstream raw materials:

(S)-4-phenyl-2-oxazolidinone

C₈H₁₄O₃

4-phenyl-2-oxazolidinone

propionic acid anhydride

Downstream raw materials:

(4S)-4-benzyl-3-(2-methylpropionyl)-2-oxazolidinone

(S)-3-[(2S,3R)-3-Hydroxy-2-methyl-5-((4R,6R)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-pentanoyl]-4-phenyl-oxazolidin-2-one

Refernces

• 1、 Zhang, Yanyan,Sun, Haopeng,You, Qidong. "Novel approach to stereoselective synthesis of (E)/(Z)-(N-acyl-oxazolidinone)-eneglycinates". . p. 749 - 760. Retrieved 2015/03/03.
• 2、 Birman, Vladimir B.,Jiang, Hui,Li, Ximin,Guo, Lei,Uffman, Eric W.. "Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation". . p. 6536 - 6537. Retrieved 2007/10/03.