(R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE

Base Information

• Chemical Name: (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE
• CAS No.: 160695-26-1
• Molecular Formula: C12H13NO3
• Molecular Weight: 219.24
• Hs Code.: 29349990
• Mol file: 160695-26-1.mol

Synonyms:2-Oxazolidinone,3-(1-oxopropyl)-4-phenyl-, (R)-;(R)-4-Phenyl-3-propionyloxazolidin-2-one;

Chemical Property of (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE

Chemical Property:

• Vapor Pressure: 2.18E-06mmHg at 25°C
• Melting Point: 83.5-84 °C(Solv: hexane (110-54-3); toluene (108-88-3))
• Refractive Index: 1.553
• Boiling Point: 393.1 °C at 760 mmHg
• PKA: -3.13±0.40(Predicted)
• Flash Point: 191.6 °C
• PSA: 46.61000
• Density: 1.223 g/cm³
• LogP: 2.05440
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

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

(R)-4-Phenyl-3-propionyloxazolidin-2-one ^*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:

Technology Process of (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE

There total 12 articles about (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE 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%

propionyl chloride (79-03-8) + (4R)-phenyl-2-oxazolidinone (90319-52-1,7480-32-2) → (4R)-3-propionyl-4-phenyl-1,3-oxazolidin-2-one (160695-26-1)

Guidance literature:

(4R)-phenyl-2-oxazolidinone; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

propionyl chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ol2023328

Reference yield: 93.0%

(4R)-phenyl-2-oxazolidinone (90319-52-1,7480-32-2) + propionic acid anhydride (123-62-6) → (4R)-3-propionyl-4-phenyl-1,3-oxazolidin-2-one (160695-26-1)

Guidance literature:

With electrogenerated base from 2-pyrrolidone; tetraethylammonium perchlorate; In acetonitrile; at 20 ℃;

DOI:10.1021/jo010038+

Reference yield: 88.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + carbon dioxide (124-38-9,18923-20-1) + (4'R)-2-bromo-1-(2'-oxo-4'-phenyloxazolidin-3'-yl)propan-1-one (201300-96-1) → (4R)-3-propionyl-4-phenyl-1,3-oxazolidin-2-one (160695-26-1) + 3-(2-methoxycarbonylpropionyl)-4R-phenyl-2-oxazolidinone

Guidance literature:

carbon dioxide; (4'R)-2-bromo-1-(2'-oxo-4'-phenyloxazolidin-3'-yl)propan-1-one; With tetrabutylammonium tetrafluoroborate; In tetrahydrofuran; at -20 ℃; under 760 Torr; Electrochemical reaction;

diazomethane; In diethyl ether;

DOI:10.1021/jo0343836

upstream raw materials:

propionyl chloride

(R)-benzyl [2-hydroxy-1-phenylethyl]carbamate

(4'R)-2-bromo-1-(2'-oxo-4'-phenyloxazolidin-3'-yl)propan-1-one

benzaldehyde

Downstream raw materials:

(4R)-4-phenyl-3-[(2R)-3,3,3-trifluoro-2-methylpropanoyl]-1,3-oxazolidin-2-one

(R)-3-((S)-2-methylpent-4-enoyl)-4-phenyloxazolidin-2-one

(3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(S)-1-((R)-4-phenyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone

(4R)-3-[(2R,3S)-3-hydroxy-2-methylpent-4-enoyl]-4-phenyl-oxazolidin-2-one

Refernces

• 1、 Reed, Carson W.,Fulton, Mark G.,Nance, Kellie D.,Lindsley, Craig W.. "Total synthesis of natural (?)- and unnatural (+)-Melearoride A". supporting information. p. 743 - 745. Retrieved 2019/02/09.
• 2、 -. "AHU - 377 preparation method of the midbody and intermediate and intermediate preparation method". Paragraph 0065; 0066; 0067; 0068. . Retrieved 2017/10/13.