(R)-4-Benzyl-2-oxazolidinone

Base Information

• Chemical Name: (R)-4-Benzyl-2-oxazolidinone
• CAS No.: 102029-44-7
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.203
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID60370594
• Nikkaji Number: J462.969H
• Wikidata: Q72441666
• ChEMBL ID: CHEMBL1366601
• Mol file: 102029-44-7.mol

Synonyms:(R)-4-Benzyl-2-oxazolidinone;102029-44-7;(R)-(+)-4-Benzyl-2-oxazolidinone;(r)-4-benzyloxazolidin-2-one;(4R)-4-benzyl-1,3-oxazolidin-2-one;2-Oxazolidinone, 4-(phenylmethyl)-, (4R)-;(r)-(-)-4-benzyl-2-oxazolidinone;MFCD00010846;4-Benzyl-1,3-oxazolidin-2-one #;(R)-4-benzyl-oxazolidin-2-one;r-4-benzyl-2-oxazolidinone;MLS001242802;4(R)-benzyl-2-oxazolidinone;4alpha-Benzyl-2-oxazolidinone;SCHEMBL137215;4-(r)-benzyl-2-oxazolidinone;4-(R)-benzyloxazolidin-2-one;(R)-4-benzyl-oxazolidin-2-on;(R)-4-benzyloxazolidine-2-one;CHEMBL1366601;(R)-4-benzyl oxazolidin-2-one;DTXSID60370594;(R) -4-benzyl-oxazolidin-2-one;HMS2205P17;r-(-)-4-benzyl-2-oxazolidinone;(R)-(+)4-benzyl-2-oxazolidinone;BCP22798;* (R)-4-Benzyl-2-oxazolidinone;AKOS005145805;AKOS015839026;(4R)-(+)-4-benzyl-2-oxazolidinone;(R)-4-(phenylmethyl)-2-oxazolidinone;(R)-4-Benzyl-2-oxazolidinone, 99%;AC-1396;BCP9000029;CS-W007664;FS-2114;(R)-(+/-)-4-benzyl-2-oxazolidinone;BP-12372;DS-14383;SMR000841429;A1783;AM20060480;B1786;(4r)-4-(phenylmethyl)-1,3-oxazolidin-2-one;EN300-267860;A1-00440;Q-102351

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

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.43E-06mmHg at 25°C
• Melting Point: 87-90 °C
• Refractive Index: 14.5 ° (C=5, MeOH)
• Boiling Point: 398.8 °C at 760 mmHg
• PKA: 12.78±0.40(Predicted)
• Flash Point: 195 °C
• PSA: 38.33000
• Density: 1.176 g/cm³
• LogP: 1.66630
• Storage Temp.: 0-6°C
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Slightly)
• Water Solubility.: Insoluble in water. Soluble in Chloroform.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 187

Purity/Quality:

99% ^*data from raw suppliers

(R)-4-Benzyl-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NC(=O)O1)CC2=CC=CC=C2
• Isomeric SMILES: C1[C@H](NC(=O)O1)CC2=CC=CC=C2
• Description: (R)-4-Benzyl-2-oxazolidinone is a derivative of oxazolidinone. It can be used in the preparation of enantiopure carbocyclic nucleosides, which act as a HIV protease inhibitor. It can also be used as a chiral auxiliary in the enantioselective synthesis of (2R, 2′S)-erythro-methylphenidate, beta-lactams and alpha-amino acids. Its end product includes asymmetric single isomeric drugs such as antitumor, anesthetic and entipasmodic products.
• Uses: An oxazolidinone used in chiral auxiliary asymetric synthesis intermediate for Aliskiren hemifumarate, Darifenacin HBr, Zolmitriptan (R)-(+)-4-Benzyl-2-oxazolidinones are used in the enantioselective synthesis of beta-lactams and alpha-amino acids. End products can include asysmmetric single isomeric drugs of antitumor, anesthetic, antipasmodic products. Used in the synthesis of HIV protease inhibitors. An oxazolidinone used in chiral auxiliary asymetric synthesis.

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

There total 94 articles about (R)-4-Benzyl-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%

N-tert-butoxycarbonyl-D-Phenylalaninol (106454-69-7) → (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7)

Guidance literature:

With thionyl chloride; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1016/S0040-4020(96)01077-0

Reference yield: 97.0%

carbon dioxide (124-38-9,18923-20-1) + (R)-2-amino-3-phenylpropanol (5267-64-1) → (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7)

Guidance literature:

With triethylamine; chlorophosphoric acid diphenyl ester; In acetonitrile; at -40 - 25 ℃;

DOI:10.1021/jo100268n

Reference yield: 96.0%

(R)-3-((2R,4R)-2-Azido-4-methyl-hexanoyl)-4-benzyl-oxazolidin-2-one (221293-03-4) → (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) + (2R,4R)-2-Azido-4-methyl-hexanoic acid (221293-04-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 0.5h;

upstream raw materials:

4-methoxy-1,3-oxazolidin-2-one

benzylmagnesium chloride

(S)-4-Benzyl-3-[(2S,3R,4R,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6,8-dimethoxy-2-(4-methoxy-benzyloxy)-4,10-dimethyl-11-triisopropylsilanyloxy-undecanoyl]-oxazolidin-2-one

2-benzylaziridine

Downstream raw materials:

(4R)-3-(3'R)-3'-(phenylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone

(S)-4-Benzyl-3-((1S,2R,4R)-2-methoxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbonyl)-oxazolidin-2-one

(R)-4-Benzyl-3-((1S,2R,4R)-2-methoxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbonyl)-oxazolidin-2-one

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

Refernces

• 1、 Saliu, Francesco,Putomatti, Benedetto,Rindone, Bruno. "Nitrogen-containing organobases as promoters in the cobalt(II)-Schiff base catalyzed oxidative carbonylation of amines". . p. 3590 - 3593. Retrieved 2012.
• 2、 Liu, Jian-Ming,Peng, Xin-Gao,Liu, Jian-Hua,Zheng, Shu-Zhan,Sun, Wei,Xia, Chun-Gu. "Synthesis of 2-oxazolidinones by salen-Co-complexes catalyzed oxidative carbonylation of β-amino alcohols". . p. 929 - 932. Retrieved 2007.
• 3、 Paz, Jairo,Pérez-Balado, Carlos,Iglesias, Beatriz,Mu?oz, Luis. "Carbonylation with CO2 and phosphorus electrophiles: A convenient method for the synthesis of 2-oxazolidinones from 1,2-amino alcohols". . p. 395 - 398. Retrieved 2009.
• 4、 Jones, Simon,Selitsianos, Dimitrios. "Stereochemical consequences of the use of chiral N-phosphoryl oxazolidinones in the attempted kinetic resolution of bromomagnesium alkoxides". . p. 3128 - 3138. Retrieved 2005.
• 5、 Chen, Yuesu,Hone, Christopher A.,Gutmann, Bernhard,Kappe, C. Oliver. "Continuous Flow Synthesis of Carbonylated Heterocycles via Pd-Catalyzed Oxidative Carbonylation Using CO and O2 at Elevated Temperatures and Pressures". . p. 1080 - 1087. Retrieved 2017.
• 6、 Yang, Qihao,Peng, Huaitao,Zhang, Qiuju,Qian, Xu,Chen, Xu,Tang, Xuan,Dai, Sheng,Zhao, Jiajun,Jiang, Kun,Yang, Qiu,Sun, Jian,Zhang, Linjuan,Zhang, Nian,Gao, Honglin,Lu, Zhiyi,Chen, Liang. "Atomically Dispersed High-Density Al–N4 Sites in Porous Carbon for Efficient Photodriven CO2 Cycloaddition". . . Retrieved 2021/09/20.