102029-44-7

Basic information

• Product Name: (R)-4-Benzyl-2-oxazolidinone
• Synonyms: 4-benzyl-2-0xazolidinone;(R)-4-BENZYL-2-OXAZOLIDINONE HPLC 99+%;(R)-4-BENZYL-2-OXAZOLIDINONE 98.0%;(4R)-Phenylmethyl-2-oxazolidinone;(4R)-4-(Phenylmethyl)-1,3-oxazolidin-2-one;(4R)-4-(Phenylmethyl)-2-oxazolidinone;(4R)-Benzyloxazolidin-2-one;(R)-4-Benzyl-2-oxazolidinone, 99%, ee:>99%
• CAS NO: 102029-44-7
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• EINECS: -0
• Product Categories: Oxazolidinone;Chiral Compounds;chiral;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Chiral chemicals;Ketone;Peptide;Aromatics;Chiral Reagents;Heterocycles;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 102029-44-7.mol
• Article Data: 73

Chemical Properties

• Melting Point: 88-90 °C
• Boiling Point: 309.12°C (rough estimate)
• Flash Point: 195 °C
• Appearance: White to almost white/Crystalline Powder
• Density: 1.1607 (rough estimate)
• Vapor Pressure: 1.43E-06mmHg at 25°C
• Refractive Index: 14.5 ° (C=5, MeOH)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly)
• PKA: 12.78±0.40(Predicted)
• Water Solubility: Insoluble in water. Soluble in Chloroform.
• Sensitive: Hygroscopic
• BRN: 4782551
• CAS DataBase Reference: (R)-4-Benzyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-Benzyl-2-oxazolidinone(102029-44-7)
• EPA Substance Registry System: (R)-4-Benzyl-2-oxazolidinone(102029-44-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 102029-44-7(Hazardous Substances Data)

Usage

Description

(R)-4-Benzyl-2-oxazolidinone is a derivative of oxazolidinone, characterized by its white to light yellow crystal powder appearance. It is a versatile compound that can be utilized in the preparation of enantiopure carbocyclic nucleosides, which serve as HIV protease inhibitors. Additionally, it is employed as a chiral auxiliary in the enantioselective synthesis of various pharmaceutical compounds, including (2R, 2′S)-erythro-methylphenidate, beta-lactams, and alpha-amino acids. Its end products encompass asymmetric single isomeric drugs such as antitumor, anesthetic, and antipasmodic agents.

Uses

Used in Pharmaceutical Industry:
(R)-4-Benzyl-2-oxazolidinone is used as a chiral auxiliary in the enantioselective synthesis of various pharmaceutical compounds for [application reason] the creation of enantiopure carbocyclic nucleosides, which act as HIV protease inhibitors, and the synthesis of (2R, 2′S)-erythro-methylphenidate, beta-lactams, and alpha-amino acids.
Used in Asymmetric Synthesis:
(R)-4-Benzyl-2-oxazolidinone is used as a chiral auxiliary in asymmetric synthesis for [application reason] the production of enantiopure compounds, which are essential in the development of single isomeric drugs with specific therapeutic effects.
Used in the Synthesis of Aliskiren Hemifumarate, Darifenacin HBr, and Zolmitriptan:
(R)-4-Benzyl-2-oxazolidinone is used as an intermediate in the synthesis of specific pharmaceutical compounds such as Aliskiren hemifumarate, Darifenacin HBr, and Zolmitriptan for [application reason] the development of drugs with targeted therapeutic effects and improved pharmacological properties.
Used in the Enantioselective Synthesis of Beta-lactams and Alpha-amino Acids:
(R)-4-Benzyl-2-oxazolidinone is used in the enantioselective synthesis of beta-lactams and alpha-amino acids for [application reason] the creation of end products that include asymmetric single isomeric drugs with antitumor, anesthetic, and antipasmodic properties, enhancing the efficacy and selectivity of these medications.

References

http://www.sigmaaldrich.com/catalog/product/aldrich/300977? lang=en?ion=US https://www.alfa.com/en/catalog/A16770/ Shieh, Wen Chung, et al. "Synthesis of enantiomerically enriched 4- piperidinylglycine." US, US 6670477B2. 2003.

InChI:InChI=1/C10H11NO2/c12-10-11-9(7-13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,12)/t9-/m1/s1

Upstream product

• 14441-94-2 4-methoxy-1,3-oxazolidin-2-one 
• 6921-34-2 benzylmagnesium chloride 
• 201230-82-2 carbon monoxide 
• 1795-98-8 rac-phenylalaninol 
• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 105-58-8 Diethyl carbonate 
• 275378-91-1 ((R)-1-Hydroxymethyl-2-phenyl-ethyl)-urea 
• 124-38-9 carbon dioxide 
• 862423-77-6 (4R)-3-[(2R,3R)-3-hydroxy-5-phenyl-2-(phenylmethoxy)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 96-49-1 [1,3]-dioxolan-2-one 

Downstream Products

• 129952-14-3 (R)-4-benzyl-3-(2-methoxyacetyl)oxazolidin-2-one 
• 128677-90-7 (4R)-3-(3'R)-3'-(phenylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone 
• 142673-42-5 (S)-4-Benzyl-3-((1S,2R,4R)-2-methoxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbonyl)-oxazolidin-2-one 
• 142673-32-3 (R)-4-Benzyl-3-((1S,2R,4R)-2-methoxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbonyl)-oxazolidin-2-one 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 123731-43-1 (R)-4-Benzyl-3-[(2E,7E,9E)-13-(4-methoxy-phenoxy)-trideca-2,7,9-trienoyl]-oxazolidin-2-one 
• 128677-87-2 (4S)-N-[(3S)-phenylbutanoyl]-4-phenylmethyl-1,3-oxazolidin-2-one 
• 148043-78-1 (4R)-3-(4,4-difluoro-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidinone 
• 148043-76-9 (4R)-3-(5,5-difluoro-1-oxohexyl)-4-(phenylmethyl)-2-oxazolidinone 
• 148043-77-0 (4R)-3-(4,4,5,5,5-pentafluoro-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidinone 
• 148043-75-8 (4R)-3-(5,5,6,6,6-pentafluoro-1-oxohexyl)-4-(phenylmethyl)-2-oxazolidinone 
• 148043-74-7 (4R)-3-(4,4,5,5,6,6,6-heptafluoro-1-oxohexyl)-4-(phenylmethyl)-2-oxazolidinone 
• 150126-86-6 (R)-N-<<3(R)-<(acetylthio)methyl>-2-oxo-1-azacyclodec-10(S)-yl>carbonyl>-4-benzyl-2-oxazolidinone 

Relevant articles and documents

Auxiliary-controlled diastereoselective synthesis of a syn C-6-epimer of the ADAM 10 inhibitor GI254023X

ADAM10 is a cell surface-expressed metalloprotease involved in various cell adhesion and proteolytic processes, in which biological studies have linked an over-expression of ADAM10 to the development and progression of various types of diseases including cancer. GI254023X is a hydroxamate metalloprotease inhibitor known for ADAM10 activity inhibition, but for which structure-activity based biological information for assessing anti-tumour and anti-inflammatory activity is lacking. In this work, an Evans’ asymmetric boron aldol reaction was used to synthesise a syn C-6-epimer of GI254023X intended for biological evaluation against the natural inhibitor.

Racemic auxiliaries: Applications to asymmetric synthesis

Racemic auxiliaries have been successfully used to achieve asymmetric synthesis. Racemic Evans aldol products were obtained from racemic acyl oxazolidinones with good diastereocontrol. The enantiomers of the racemic aldol products were resolved by a lipase-catalysed acylation reaction. Hydrolysis afforded enantiomerically enriched oxazolidinones and enantiomerically enriched β-hydroxy acids.

Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 1: Synthetic Strategy and Preparation of a Common Precursor

The synthetic strategy for producing multigram quantities of (+)-discodermolide (1) using a hybridized Novartis-Smith-Paterson synthetic route via common precursor 3 is described. In the first part of this five-part series, we present a multikilogram preparation of α-methyl aldehyde 10 from Roche ester, its syn-aldol reaction with Evans boron enolate, removal of the chiral auxiliary, and the preparation of Weinreb amide 3 (Smith common precursor). The common precursor was produced without any chromatography.

Direct catalytic asymmetric α-amination of aldehydes

The first direct catalytic asymmetric α-amination of aldehydes is described herein. α-Unbranched aldehydes react in this novel proline-catalyzed reaction with dialkyl azodicarboxylates to give α-amino aldehydes in excellent yields and enantioselectivities. Copyright

Synthesis of chiral oxazolidin-2-ones and imidazolidin-2-ones via DMAP- catalyzed isocyanation of amines with di-tert-butyl dicarbonate

Oxazolidin-2-ones and imidazolidin-2-ones are prepared under mild reaction conditions by DMAP-catalyzed isocyanation of 1,2-aminoalcohols and 1,2-diamines with di-tert-butyl dicarbonate and subsequent cyclization.

Room Temperature Cu-Catalyzed N-Arylation of Oxazolidinones and Amides with (Hetero)Aryl Iodides

N,N′-Bis(pyridin-2-ylmethyl)oxalamide (BPMO) was found to be an apposite promoter for the Cu-catalyzed N-arylation of oxazolidinones and primary and secondary amides with (hetero)aryl iodides at room temperature. Excellent chemoselectivity reached between

Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety

Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.