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Synthesis 1993; 1993(9): 861-863
DOI: 10.1055/s-1993-25956
short paper
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Equilibrium Control in Bromomethylation: An Expedient Route to 2-Amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic Acid (AMPA)

Mikael Begtrup* , Frank A. Sløk
  • *Department of Organic Chemistry, Royal School of Pharmacy, Universitetsparken 2, DK-2100 Copenhagen, Denmark
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Publication Date:
29 April 2002 (online)

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The excitatory amino acid 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) has been prepared in gram quantities in 42% total yield by a three-step procedure from 3-hydroxy-5-methylisoxazole. It is shown how bromomethylation may be optimized through control of the involved equilibria and how N-protecting methoxymethyl groups can be removed.