Analysis Note

Color (visual): white to yellow to beigeAppearance of substance (visual): beadsLoading / photometric determination of p-nitrophenol released upon treatment with piperidine / DMF: 0.60 - 1.20 mmol/gSwelling Volume (in DMF): lot specific resultThe polymer matrix is copoly (styrene - 1% DVB ), 100 - 200 mesh.

General description

Resin-bound p-nitrophenyl carbonate esters react readily with amines to provide the corresponding resin-bound carbamate. Leznoff [1] was the first to demonstrate the utility of such resins in solid phase synthesis with the preparation of mono-acylated diamines from symmetrical diamines.

Similarly, Dressman, et al. [2] have used carbamate linked resin-bound amino acid amides to make hydantoins via a base-mediated cyclization/cleavage strategy.

Amines linked to p-nitrophenyl carbonate Wang resin possess similar chemical properties to methoxybenzyloxycarbonyl protected amines. The resin-bound carbamate is, therefore, cleaved with TFA or hydrogenolysis to afford the free amine [3]. Alternatively, cleavage by reduction with lithium aluminium hydride can be used to generate N-methylamines [4], and Raju & Kogan [5] have utilized this resin to prepare sulfonamides by acylation of immobilized arylamines and cleavage with LiOH or NaOMe. An analogous p-nitrophenyl carbonate resin prepared from NovaSyn™ TGA resin was employed as a support for the solid phase immobilization of amidines [6]. This resin was also used to synthesize polyamines [7, 8], and to immobilize indoles [9] and guanidinylating reagents [10].

Loading of this resin can be quantified by measuring the release of p-nitrophenolate [11].

The product number for this product was previously 01-64-0123.

To obtain a certificate of analysis (CoA) of a lot that begins with the letter “A”, please select the option in the right hand menu “Request a COA for Lot#s starting with A”.

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Linkage

Replaces: 01-64-0123