Abstract
A new, mild, general, and efficient synthesis of N-protected α-amino
acid hydrazides is described. This two-step preparation uses N-aminophthalimide as protected hydrazine
to prepare N-protected α-amino acid hydrazide precursors,
and subsequent dephthaloylation with an aminomethyl polystyrene
resin yields N-protected α-amino acid hydrazides. It has
the advantages of avoiding the use of the toxic hydrazine reagent
and being compatible with the most commonly used N-protecting groups.
This strategy is particularly interesting in the case of N-(9-fluorenylmethoxycarbonyl)-protected
amino acids. Within the limits of chiral HPLC detection, no epimerization
is apparent.
Key words
amino acids - hydrazides - epimerization - protecting groups - aminomethyl resins
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