102029-44-7

Usage

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 
• 126821-31-6 (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 
• 13906-90-6 2-benzylaziridine 
• 124-38-9 carbon dioxide 
• 189760-91-6 (4S)-3-[(2R)-4-cyano-2-ethyl-1-oxobutan-1-yl]-4-(phenylmethyl)-1,3-oxazolidin-2-one 
• 201230-82-2 carbon monoxide 
• 3182-95-4 L-Phenylalaninol 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 
• 1795-98-8 rac-phenylalaninol 
• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 300-57-2 allylbenzene 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 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 
• 214492-00-9 (4R)-4-benzyl-3-[(2R)-2-phenylpropionyl]oxazolidin-2-one 
• 143761-23-3 (+)-4S-3-[1'-oxo-6'-(benzyloxy)hexyl]-4-benzyl-2-oxazolidinone 

Relevant academic research and scientific papers

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.

Nitrogen-containing organobases as promoters in the cobalt(II)-Schiff base catalyzed oxidative carbonylation of amines

The use of organic bases as promoters in the cobalt(II)-Schiff base complex catalyzed oxidative carbonylation of amines was investigated. The generality of the reaction was also studied by submitting different amines to the same procedure and by changing the reaction conditions. Very good yields in the corresponding ureas were achieved in toluene with a catalyst loading of 0.5 mol % and using TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene) as promoter. Methyl carbamates were obtained in methanol.

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.

Synthesis of 2-oxazolidinones by salen-Co-complexes catalyzed oxidative carbonylation of β-amino alcohols

2-Oxazolidinones are synthesized in high yield by oxidative carbonylation of β-amino alcohols using salen-Co(II)/NaI or salen-Co(III)-I as a catalyst and using CO as the carbonyl source. Studies of functional group compatibility using a series of substituted salen-Co(II) or salen-Co(III)-I complexes demonstrate a broad tolerance of functionality during the carbonylation reaction.

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.

Carbonylation with CO2 and phosphorus electrophiles: A convenient method for the synthesis of 2-oxazolidinones from 1,2-amino alcohols

2-Oxazolidinones were prepared in good yields from 1,2-amino alcohols and CO2 in the presence of tetramethyl-phenylguanidine (PhTMG) as a base and a variety of phosphorus electrophiles under mild conditions. This procedure is advantageous over previous methodologies and relies on a novel carbonylation procedure that utilizes nontoxic CO2 and phosphorus electrophiles. Georg Thieme Verlag Stuttgart.

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

Stereochemical consequences of the use of chiral N-phosphoryl oxazolidinones in the attempted kinetic resolution of bromomagnesium alkoxides

A number of chiral N-phosphoryl oxazolidinones have been prepared and evaluated as asymmetric phosphoryl transfer agents with the magnesium alkoxide of 1-phenyl ethanol. The reaction proceeded with little stereoselection, which was shown to be a consequence of the reaction mechanism that occurs with inversion of configuration at phosphorus consistent with in-line attack opposite the leaving group.

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.

Continuous Flow Synthesis of Carbonylated Heterocycles via Pd-Catalyzed Oxidative Carbonylation Using CO and O2 at Elevated Temperatures and Pressures

A continuous-flow Pd-catalyzed oxidative carbonylation protocol utilizing CO and O2 gas for the synthesis of carbonylated heterocycles is described. The optimization of temperature, pressure, CO/O2 ratio, catalyst loading, and reaction time resulted in process intensified conditions for this transformation. The optimized continuous flow conditions (120 °C, 20 bar pressure, 24 min residence time) were used to prepare a number of benzoxazolone, 2-benzoxazolidinone, and other biologically and synthetically important five- and six-membered carbonylated heterocycles in good overall yield and purity (14 examples). The continuous-flow process enables the safe and scalable oxidative carbonylation using CO/O2 under elevated pressures and temperatures.