N-Phenyl-(5R)-hydroxyMethyl-2-oxazolidinone

Base Information

• Chemical Name: N-Phenyl-(5R)-hydroxyMethyl-2-oxazolidinone
• CAS No.: 87508-42-7
• Molecular Formula: C10H11NO3
• Molecular Weight: 193.202
• Mol file: 87508-42-7.mol

Synonyms:(R)-5-(hydroxymethyl)-3-phenyloxazolidin-2-one;

Chemical Property of N-Phenyl-(5R)-hydroxyMethyl-2-oxazolidinone

Chemical Property:

• PSA: 49.77000
• LogP: 1.06910

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-Phenyl-(5R)-hydroxyMethyl-2-oxazolidinone

There total 13 articles about N-Phenyl-(5R)-hydroxyMethyl-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: 95.0%

N-phenyl methyl carbamate (2603-10-3) + (R)-glycidyl butyrate (60456-26-0) → (R)-5-(hydroxymethyl)-3-phenyl-2-oxooxazolidine (87508-42-7)

Guidance literature:

N-phenyl methyl carbamate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.63333h;

(R)-glycidyl butyrate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 22.1h;

DOI:10.15227/orgsyn.081.0112

Reference yield: 76.0%

(R)-3-(phenylamino)-1,2-propanediol (87508-50-7) + Diethyl carbonate (105-58-8,76619-83-5) → (R)-5-(hydroxymethyl)-3-phenyl-2-oxooxazolidine (87508-42-7)

Guidance literature:

With sodium methylate; In toluene; Heating;

DOI:10.1021/jm00128a003

Reference yield: 70.0%

carbon dioxide (124-38-9,18923-20-1) + C9H11NO → (R)-5-(hydroxymethyl)-3-phenyl-2-oxooxazolidine (87508-42-7)

Guidance literature:

With dmap; C₂₀H₁₄AlNO₃; In dichloromethane; at 25 ℃; for 24h; under 760.051 Torr; stereoselective reaction; Sealed tube;

DOI:10.1021/acs.orglett.8b02186

upstream raw materials:

(R)-3-(phenylamino)-1,2-propanediol

Diethyl carbonate

N-(benzyloxycarbonyl)aniline

(R)-glycidyl butyrate

Downstream raw materials:

Methanesulfonic acid (R)-2-oxo-3-phenyl-oxazolidin-5-ylmethyl ester

(R)-2-<(3-phenyl-2-oxo-5-oxazolidinyl)methyl>phthalimide

(R)-4-[5-(hydroxymethyl)-2-oxo-3-oxazolidinyl]benzenesulfonamide

(R)-5-(fluoromethyl)-3-phenyl-2-oxooxazolidine

Refernces

• 1、 Ali, Akbar,Reddy, G. S. Kiran Kumar,Cao, Hong,Anjum, Saima Ghafoor,Nalam, Madhavi N. L.,Schiffer, Celia A.,Rana, Tariq M.. "Discovery of HIV-1 protease inhibitors with picomolar affinities incorporating N-aryl-oxazolidinone-5-carboxamides as novel P2 ligands". . p. 7342 - 7356. Retrieved 2007/10/03.
• 2、 Lohray, Braj B.,Baskaran, Sundarababu,Rao, B. Srinivasa,Reddy, B. Yadi,Rao, I. Nageswara. "A short synthesis of oxazolidinone derivatives linezolid and eperezolid: A new class of antibacterials". . p. 4855 - 4856. Retrieved 2007/10/03.