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Biotage® PS-TEMPO

Self-Indicating TEMPO Oxidation, Reusable and No Work-up Required

PS-TEMPO

Biotage® PS-TEMPO is a novel polymer bound oxidant, based on a polystyrene bound, sulfonic ester linked 2,2,6,6-tetramethylpiperidine-1-oxyl species (PS-TEMPO),. It allows rapid and efficient access to often unstable ketone or aldehyde reactive species, and displays a visual indication of its oxidation state. The color change observed as the oxidation state of the reagent changes, can give an indication of the extent to which the reagent has been used. PS-TEMPO can be regenerated and reused for multiple oxidation reactions.

CONSUMABLES

Part No. Description Product type Pack Size Price
800520 Biotage® PS-TEMPO, 10 g Consumables 1 Log in for price
800521 Biotage® PS-TEMPO, 25 g Consumables 1 Log in for price
800522 Biotage® PS-TEMPO, 100 g Consumables 1 Log in for price
800523 Biotage® PS-TEMPO, 1 kg Consumables 1 Log in for price
800524 Biotage® PS-TEMPO, 3 g Consumables 1 Log in for price

Committed to preserving our shared environment – further details available on request.

Can be used in processes in compliance with cGMP standards.

Manufacture of consumables is accredited by the world renowned British Standards Institute.

Flexible supply chains, back up manufacturing and warehousing ensures supply risk reduction

Can be used in processes in compliance with GLP standards.

Products which are scaleable from lab or development to process scale.

Long to indefinite product shelf life, reduced process risk.

Supports pharma guidelines for reducing elemental impurities in APIs.

Further extractable information provided on request.

Raw materials certified free of materials of human or animal origin.

Chemical substances used in our manufacturing process do not require registration.

Able to withstand mechanical stirring and heating under normal reaction conditions.

Download the product note.

 

Background

Biotage® PS-TEMPO is a novel polymer bound oxidant, based on a polystyrene bound, sulfonic ester linked 2,2,6,6-tetramethylpiperidine-1-oxyl species (PS-TEMPO). It allows rapid and efficient access to often unstable ketone or aldehyde reactive species, for use in subsequent chemical reactions. The material has fast room temperature kinetics compared to similar known systems,1,2 displays a visual indication of its oxidation state and can be regenerated and reused for multiple oxidation reactions. The color change observed as the oxidation state of the reagent changed, can give an indication of the extent to which the reagent has been used.

Activation and Recycling

Activation of the PS-TEMPO was performed by treating the material with chlorine which was produced by adding a solution of HCl in dioxane to N-chlorosuccinimide. The yellow colored inactive resin turned a deep red at activation.

Oxidation

The alcohol, dissolved in an appropriate solvent, was added to an excess of the activated PS-TEMPO reagent, typically 2.5 equivalents, and the mixture was gently swirled at room temperature. Samples were taken from the mixture and analyzed by LC-MS. When the reaction was completed the resin, now yellow colored, was filtered off, washed and the solvents were removed in vacuo. The residue was weighed and analyzed. For Further details please see product note PPS388.

General Experimental Procedure

Activation

3.0 ml (3 equiv.) of a 1.07 M filtered solution of N-chlorosuccinimide in DCM:MeCN (1:1) and 0.8 ml (3 equiv.) 4 M HCl in dioxane was added to 0.5 g PS-TEMPO (2.11 mmol/g). The mixture was swirled gently at room temperature for 10 min. The resin was filtered off, washed 5 times with 4 mL DCM:MeCN (1:1) and then directly used in the oxidation step.

Oxidation

0.5 g activated PS-TEMPO (1.06 mmol, 2.5 equiv.) was added to 0.422 mmol alcohol dissolved in 2.5 ml DCM:MeCN (1:1). The mixture was swirled gently at room temperature and samples were taken from the mixture for LC-MS analysis every 30 min. When the oxidation had ceased, the resin was filtered off and washed 5 times with 2.5 mL DCM:MeCN, (1:1). The solvent were removed in vacuo from the combined filtrate and washings. The residue was weighed and analyzed by LC-MS at an appropriate wavelength and 1H NMR.