A convenient two step transformation of tyrosine into the antihypertensive amino acid (S)-4-hydroxy-3-hydroxymethylphenylalanine

Add time:09/05/2019    Source:sciencedirect.com

Treatment of tyrosine with paraformaldehyde and catalytic amounts of p-toluenesulfonic acid, at reflux in toluene, directly generates benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate, which on treatment with boron trichloride in dichloromethane, affords (S)-4-hydroxy-3-hydroxymethylphenylalanine.

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