ePrints

A new strategy for the synthesis of taurine derivatives using the 'safety-catch' principle for the protection of sulfonic acids

Lookup NU author(s): Sonja Seeberger, Professor Roger Griffin, Dr Ian HardcastleORCiD, Emeritus Professor Bernard Golding

Downloads

Full text for this publication is not currently held within this repository. Alternative links are provided below where available.

Abstract

The safety-catch principle has been applied for the development of a new method for protecting sulfonic acids. 2,2-Dimethylsuccinic acid was reduced to 2,2-dimethylbutane-1,4-diol, which was selectively silylated to give 4-(tert-butyldiphenylsilanyloxy)-2,2-dimethylbutan-1-ol. Reaction of the latter compound with 2-chloroethanesulfonyl chloride in the presence of triethylamine afforded 4-(tert-butyldiphenylsilyloxy)-2,2-dimethylbutyl ethenesulfonate directly. The ethenesulfonate underwent Michael-type addition with secondary amines to give protected derivatives of taurine (2-aminoethanesulfonic acid). Deprotection was achieved on treatment with tetrabutylammonium fluoride, whereby cleavage of the silicon - oxygen bond led to an intermediate alkoxide that immediately cyclised to 2,2-dimethyltetrahydrofuran with liberation of a sulfonate. Pure sulfonic acids were obtained from the crude product by ion exchange chromatography on a strongly basic resin, which was eluted with aqueous acetic acid. The method developed should be generally applicable to the protection of sulfonic acids and is amenable to a multiparallel format.

Publication metadata

Author(s): Seeberger S, Griffin RJ, Hardcastle IR, Golding BT

Publication type: Article

Publication status: Published

Journal: Organic & Biomolecular Chemistry

Year: 2007

Volume: 5

Issue: 1

Pages: 132-138

Date deposited: 12/05/2010

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

URL: http://dx.doi.org/10.1039/b614333d

DOI: 10.1039/b614333d

PubMed id: 17164917

Altmetrics

Share