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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 Hardcastle, Professor Bernard Golding

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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


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