63160-13-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine is used as an oxidizing agent for the preparation of a wide variety of pharmaceutical compounds. Its ability to selectively oxidize various functional groups, such as alcohols and amines, makes it a versatile and valuable tool in the synthesis of complex molecules, including those with potential therapeutic applications.
Used in Organic Chemistry:
In the field of organic chemistry, 3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine is employed as a reagent for the oxidation of various substrates, including alcohols, amines, and sulfides. Its selective oxidation properties allow chemists to introduce new functional groups into molecules, enabling the synthesis of a diverse range of compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine is also utilized in research and development settings, where it serves as a key reagent for the synthesis of novel compounds and the investigation of new reaction mechanisms. Its unique properties and reactivity make it an essential tool for chemists working on the design and synthesis of new molecules with potential applications in various fields.

InChI:InChI=1/C13H11NO3S/c15-18(16,12-9-5-2-6-10-12)14-13(17-14)11-7-3-1-4-8-11/h1-10,13H

Synthetic route

(S)-4-benzyl-3-{3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionyl}oxazolidin-2-one (959937-89-4) → (S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4)

Conditions	Yield
Stage #1: (S)-4-benzyl-3-{3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionyl}oxazolidin-2-one With sodium hexamethyldisilazane In tetrahydrofuran at -78 - -40℃; for 0.75h; Stage #2: With N-(benzenesulfonyl)-3-phenyloxaziridine In tetrahydrofuran at -78℃; for 2h;
Stage #1: (S)-4-benzyl-3-{3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionyl}oxazolidin-2-one With sodium hexamethyldisilazane In tetrahydrofuran at -78 - -40℃; for 0.75h; Stage #2: With N-(benzenesulfonyl)-3-phenyloxaziridine In tetrahydrofuran at -78℃; for 2h;

3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionic acid (959937-90-7) → (S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / diethyl ether; dichloromethane / 1.08 h / -78 - 0 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C 2.2: 3 h / -78 - 20 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 - -40 °C 3.2: 2 h / -78 °C View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / diethyl ether; dichloromethane / 1.08 h / -78 - 0 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C 2.2: 3 h / -78 - 20 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 - -40 °C 3.2: 2 h / -78 °C View Scheme

C28H37NO7S → (S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C 1.2: 3 h / -78 - 20 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 - -40 °C 2.2: 2 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C 1.2: 3 h / -78 - 20 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 - -40 °C 2.2: 2 h / -78 °C View Scheme

(S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4) + trimethoxonium tetrafluoroborate (420-37-1) → (S)-4-benzyl-3-{(S)-2-methoxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (1005478-61-4)

Conditions	Yield
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In dichloromethane at 0 - 20℃; for 3h; Molecular sieve;

(S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4) → (S)-4-benzyl-3-{(S)-2-methoxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (1005478-61-4)

Conditions	Yield
With trimethoxonium tetrafluoroborate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In dichloromethane at 0 - 20℃; Molecular sieve;

Upstream product

• 13909-34-7 N-benzylidenephenylsulfonamide 
• 959937-90-7 3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionic acid 
• 959937-89-4 (S)-4-benzyl-3-{3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionyl}oxazolidin-2-one 

Downstream Products

• 1005478-61-4 (S)-4-benzyl-3-{(S)-2-methoxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one 

Relevant academic research and scientific papers

SUBSTITUTED PIPERIDINES AS THERAPEUTIC COMPOUNDS

Use of compounds of the general formula (I) and pharmaceutically acceptable salt thereof, in which R, R1 and X have the definitions illustrated in detail in the description, as beta-secretase, cathepsin D, plasmepsin Il and/or HIV protease inhibitors.

2,5-DISUBSTITUTED PIPERIDINES

The application relates to 2,5-disubstituted piperidines, their preparation and use as medicines, especially as renin inhibitors, of the general formula (I) in which R, R1 and X are each as defined in detail in the description, and pharmaceutical preparations comprising these compounds.

ASYMMETRIC SYNTHESIS AND STEREOCHEMICAL PROPERTIES OF OPTICALLY ACTIVE N-SULPHONYL-3-ARYLOXAZIRIDINES

Oxidation of prochiral sulphonimines (RSO2N = CHAr) with (1S)-(+)-PCA, followed by fractional crystallization of the crude reaction products, provides highly optically-pure N-sulphonyl-3-aryloxaziridines 1H-NMR spectra recorded in the presence of chiral solvent or shift reagent, CD spectra, and the results observed by using them as new chiral oxidizing reagents, are also reported.