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

Base Information

• Chemical Name: (S)-4-Benzyl-3-propionyloxazolidin-2-one
• CAS No.: 101711-78-8
• Molecular Formula: C₁₃H₁₅NO₃
• Molecular Weight: 233.267
• Hs Code.: 29349990
• European Community (EC) Number: 640-511-1
• DSSTox Substance ID: DTXSID50369977
• Nikkaji Number: J427.172F,J3.119.297H
• Wikidata: Q72442863
• Mol file: 101711-78-8.mol

Synonyms:101711-78-8;(S)-4-BENZYL-3-PROPIONYLOXAZOLIDIN-2-ONE;(S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone;(S)-4-Benzyl-3-propionyl-2-oxazolidinone;(4S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone;(4S)-4-benzyl-3-propanoyl-1,3-oxazolidin-2-one;2-Oxazolidinone, 3-(1-oxopropyl)-4-(phenylmethyl)-, (4S)-;MFCD00269688;SCHEMBL291952;DTXSID50369977;WHOBYFHKONUTMW-NSHDSACASA-N;AKOS015839019;AKOS015889773;CS-W008304;(4S)-3-propionyl-4-benzyloxazolidinone;AC-23910;AM802842;AS-16174;BP-12594;3-Propanoyl-4beta-benzyloxazolidine-2-one;(4S)-4-Benzyl-3-propionyl-2-oxazolidinon;(4S)-N-propionyl-4-benzyl-2-oxazolidinone;4-(S)-Benzyl-3-propionyl-2-oxazolidinone;4-(S)-benzyl-3-propionyl-oxazolidin-2-one;B2166;(S)-(+)-4-Benzyl-3-propionyl-2-oxalidinone;(3S)-3-Propionyl-4beta-benzyloxazolidine-2-one;J-000484;(S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone, 99%

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

Chemical Property:

• Vapor Pressure: 1.68E-06mmHg at 25°C
• Melting Point: 42-46 °C
• Refractive Index: 103 ° (C=1, EtOH)
• Boiling Point: 396.6 °C at 760 mmHg
• PKA: -2.35±0.40(Predicted)
• Flash Point: 193.7 °C
• PSA: 46.61000
• Density: 1.206 g/cm³
• LogP: 1.92440
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform, Methanol
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 233.10519334
• Heavy Atom Count: 17
• Complexity: 297

Purity/Quality:

99% ^*data from raw suppliers

(S)-4-Benzyl-3-propionyl-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22-43
• Safety Statements: 37/39-26-36-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(=O)N1C(COC1=O)CC2=CC=CC=C2
• Isomeric SMILES: CCC(=O)N1[C@H](COC1=O)CC2=CC=CC=C2
• Uses: Versatile chiral auxiliary for asymmetric synthesis. Intermediate in the preparation of Albaconazole.

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

There total 30 articles about (S)-4-Benzyl-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: 95.0%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + propionic acid anhydride (123-62-6) → (S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8)

Guidance literature:

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

DOI:10.1021/jo010038+

Reference yield: 94.0%

1-(1H-imidazol-1-yl)propan-1-one (4122-52-5) + (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) → (3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; chemoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201203976

Reference yield: 91.0%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + propionyl chloride (79-03-8) + Diethyl carbonate (105-58-8,76619-83-5) → (S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8)

Guidance literature:

(S)-4-Benzyl-2-oxazolidinone; Diethyl carbonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

propionyl chloride; In tetrahydrofuran; hexane; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03299

upstream raw materials:

(S)-4-Benzyl-2-oxazolidinone

propionyl chloride

propionic acid

propionic acid anhydride

Downstream raw materials:

(S)-4-benzyl-3-((R,E)-2-methyl-5-phenylpent-4-enoyl)oxazolidin-2-one

<4S,3(2R)>-4-benzyl-3-<4-(tert-butoxycarbonyl)-2-methylbutanoyl>-2-oxazolidinone

<<3-(2S)-4R>-3-(2-Methyl-1,3-dioxo-pentyl)-4-(phenylmethyl)>-2-oxazolidinone

(4S)-4-benzyl-3-(2-bromopropanoyl)-1,3-oxazolidin-2-one

Refernces

• 1、 Ager, David J.,Allen, David R.,Schaad, David R.. "Simple and efficient N-acylation reactions of chiral oxazolidinone auxiliaries". . p. 1283 - 1285. Retrieved 1996.
• 2、 Ho, Guo-Jie,Mathre, David J.. "Lithium-Initiated Imide Formation. A Simple Method for N-Acylation of 2-Oxazolidinones and Bornane-2,10-Sultam". . p. 2271 - 2273. Retrieved 1995.
• 3、 Ichikawa, Satoshi,Katsuyama, Akira,Kitahata, Shun. "A Synthesis Strategy for the Production of a Macrolactone of Gulmirecin A via a Ni(0)-Mediated Reductive Cyclization Reaction". . . Retrieved 2020.
• 4、 Andrade, Carlos Kleber Z.,Rocha, Rafael O.,Vercillo, Otilie E.,Silva, Wender A.,Matos, Ricardo Alexandre F.. "DCC/DMAP-Mediated Coupling of Carboxylic Acids with Oxazolidinones and Thiazolidinethiones". . p. 2351 - 2352. Retrieved 2003.
• 5、 Yevglevskis, Maksims,Lee, Guat L.,Threadgill, Michael D.,Woodman, Timothy J.,Lloyd, Matthew D.. "The perils of rational design-unexpected irreversible elimination of fluoride from 3-fluoro-2-methylacyl-CoA esters catalysed by α-methylacyl-CoA racemase (AMACR; P504S)". . p. 14164 - 14166. Retrieved 2014.
• 6、 Jiao, Zhi-Gang,Chang, Xiao-Wei,Ding, Wei,Liu, Guo-Jun,Song, Ke-Sheng,Zhu, Nian-Yong,Zhang, Dan-Wei,Yang, Dan. "β N-O turns and helices induced by β2-aminoxy peptides: Synthesis and conformational studies". . p. 1791 - 1799. Retrieved 2011.
• 7、 N?cker, Christina,Kaiser, Nadine,Foley, Daniel,Sievers, Sonja,Janning, Petra,Waldmann, Herbert,Laraia, Luca. "Thermal proteome profiling efficiently identifies ribosome destabilizing oxazolidinones". supporting information. . Retrieved 2021/04/22.