(R)-4-Benzyl-3-chloroacetyl-2-oxazolidinone

Base Information

• Chemical Name: (R)-4-Benzyl-3-chloroacetyl-2-oxazolidinone
• CAS No.: 184714-56-5
• Molecular Formula: C12H12ClNO3
• Molecular Weight: 253.685
• European Community (EC) Number: 634-055-2
• DSSTox Substance ID: DTXSID70442170
• Nikkaji Number: J1.288.240H
• Wikidata: Q72440886
• Mol file: 184714-56-5.mol

Synonyms:184714-56-5;(R)-4-Benzyl-3-(2-chloroacetyl)oxazolidin-2-one;(R)-4-Benzyl-3-chloroacetyl-2-oxazolidinone;(4R)-4-BENZYL-3-(2-CHLOROACETYL)-1,3-OXAZOLIDIN-2-ONE;(N-Chloroacetyl)-(4R)-benzyl-2-oxazolidinone;DTXSID70442170;AKOS015911877;AS-67591;CS-0448942;E78360;3-(Chloroacetyl)-4alpha-benzyloxazolidine-2-one;A908483;(R)-4-Benzyl-3-chloroacetyl-2-oxazolidinone, 97%

Chemical Property of (R)-4-Benzyl-3-chloroacetyl-2-oxazolidinone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 78-82 °C(lit.)
• Refractive Index: 1.577
• Boiling Point: 416.232 °C at 760 mmHg
• Flash Point: 205.53 °C
• PSA: 46.61000
• Density: 1.348 g/cm³
• LogP: 1.75320
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 253.0505709
• Heavy Atom Count: 17
• Complexity: 302

Purity/Quality:

99.3% ^*data from raw suppliers

(R)-4-Benzyl-3-chloroacetyl-2-oxazolidinone 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(N(C(=O)O1)C(=O)CCl)CC2=CC=CC=C2
• Isomeric SMILES: C1[C@H](N(C(=O)O1)C(=O)CCl)CC2=CC=CC=C2

Technology Process of (R)-4-Benzyl-3-chloroacetyl-2-oxazolidinone

There total 7 articles about (R)-4-Benzyl-3-chloroacetyl-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: 100.0%

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) + chloroacetyl chloride (79-04-9) → (R)-4-benzyl-3-(2-chloroacetyl)oxazolidin-2-one (184714-56-5)

Guidance literature:

With n-butyllithium; triphenylmethane; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

DOI:10.1021/jo961554g

Reference yield: 97.0%

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) + Chloroacetic anhydride (541-88-8) → (R)-4-benzyl-3-(2-chloroacetyl)oxazolidin-2-one (184714-56-5)

Guidance literature:

at 120 ℃;

DOI:10.1055/s-2000-6508

Reference yield:

N-chloroacetyl-(S)-(-)-4-benzyl-2-oxazolidinone → (4S)-(+)-3-(chloroacetyl)-4-(phenylmethyl)-2-oxazolidinone (104324-16-5) + (R)-4-benzyl-3-(2-chloroacetyl)oxazolidin-2-one (184714-56-5)

Guidance literature:

With Pirkle-type column binaphthyl diamine-derived CSP (CSP 5); In hexane; isopropyl alcohol; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/bkcs.10116

upstream raw materials:

(R)-4-(phenylmethyl)-2-oxazolidinone

chloroacetyl chloride

Chloroacetic anhydride

(R)-3-phenyl-2-ureido-propionic acid

Downstream raw materials:

(4R)-3-(bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone

N-[2-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-formamide

(4R,2'R,3'S)-4-benzyl-(2'-chloro-3'-hydroxyheptanoyl)-2-oxazolidinone

[2-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-oxoethyl]phosphonic acid diethyl ester

Refernces

• 1、 Madhu, Madasu,Doda, Sai Reddy,Begari, Prem Kumar,Dasari, Krishna Rao,Thalari, Gangadhar,Kadari, Sudhakar,Yadav, Jhillu Singh. "Enantioselective epoxidation by the chiral auxiliary approach: Asymmetric total synthesis of (+)-Ambrisentan". . p. 942 - 946. Retrieved 2021/02/26.
• 2、 Leitis, Zigmārs,Lūsis, Viesturs. "Conjugate addition of aryl nucleophiles to α,β-unsaturated cinnamic acid derivatives containing Evans type chiral auxiliaries". . p. 843 - 851. Retrieved 2016/09/02.