63160-13-4

Basic information

• Product Name: 3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE
• Synonyms: TRANS-2-(PHENYL SULFONYL)-3-PHENYL OXAZIRIDINE;3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE;Oxaziridine, 3-phenyl-2-(phenylsulfonyl;2-(benzenesulfonyl)-3-phenyloxaziridine;trans-2-(Phenylsulfonyl)-3-phenyloxyaziridine;3-Phenyl-N-phenylsulfonyloxaziridine;Davis Oxaziridine;N-(Phenylsulfonyl)phenyloxaziridine
• CAS NO: 63160-13-4
• Molecular Formula: C₁₃H₁₁NO₃S
• Molecular Weight: 261.3
• EINECS: 1533716-785-6
• Product Categories: Aromatics;Heterocycles;Intermediates;Sulfur & Selenium Compounds
• Mol File: 63160-13-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 96-97 °C
• Boiling Point: 394.4 °C at 760 mmHg
• Flash Point: 192.3 °C
• Appearance: /
• Density: 1.398 g/cm³
• Vapor Pressure: 1.99E-06mmHg at 25°C
• Refractive Index: 1.654
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: -13.47±0.40(Predicted)
• CAS DataBase Reference: 3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE(63160-13-4)
• EPA Substance Registry System: 3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE(63160-13-4)

Safety Data

• Hazardous Substances Data: 63160-13-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 63160-13-4 differently. You can refer to the following data:
1. 3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine, is an oxidizing agent used in the preparation of wide variety of pharmaceutical compounds.
2. Davis Oxaziridine is an oxidizing agent used in the preparation of wide variety of pharmaceutical compounds.

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

• 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 
• 13909-34-7 N-benzylidenephenylsulfonamide 

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 articles and documents

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