The Resolution of N-Benzyloxycarbonyl-DL-amino Acids Using Ephedrine

概要

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The use of ephedrine has here been proposed to be of value in the direct resolution of racemic N-benzyloxycarbonylamino acids. By using a half equi-amount of natural (−)-ephedrine, N-benzyloxycarbonyl derivatives of β-methyl DL-aspartate, DL-leucine, DL-methionine, and O-benzyloxycarbonyl-DL-serine resulted, each in turn producing a salt of the respective D-isomer. On the other hand, DL-isoleucine, erythro-β-methyl-DL-leucine, threo-N,β-dimethyl-DL-leucine, DL-valine, and DL-phenylalanine each produced a salt of each L-isomer with the same base. It should be better to protect, if possible, the third functional groups of three functional amino acids before the resolution. Each antipode of the optically active N-benzyloxycarbonylamino acid obtained above was also conveniently produced, in a high optical purity, by using (+)-ephedrine alternately. However, a few limitations on the desirable method of resolution have also been observed.
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