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Synthesis 2008(5): 693-695  
DOI: 10.1055/s-2008-1032164
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient and Practical Protection of the Catechol Residue of 3,4-Dihydroxyphenylalanine (DOPA) Derivative as Acetonide

Vadim A. Soloshonok*, Hisanori Ueki
Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA
e-Mail: vadim@ou.edu;
Further Information

Publication History

Received 27 September 2007
Publication Date:
08 February 2008 (online)

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Abstract

The acetonide formation of 3,4-dihydroxyphenylalanine (DOPA) derivative was realized under efficient and practical reaction conditions: the reaction of the methyl ester of DOPA in acetone-i-PrOH in the presence of 5 mol% of TsOH afforded the catechol side chain protected DOPA as an acetonide in quantitative yield; the workup procedure is a simple evaporation of the solvents. This methodology allows an access to the reaction in large scale.

Key words

3,4-dihydroxyphenylalanine (DOPA) - protection - acetonide

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