Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Racemization of Optically Active Aromatic N-Acetylamino Acids and Asymmetric Transformation of N-Acetyl-2-(4-hydroxyphenyl)glycine via Salt Formation with Optically Active α-Methylbenzylamine
Tadashi ShiraiwaShinji SakataHisashi NatsuyamaKeiko FujishimaHideya MiyazakiSatoru KuboTomohisa NittaHidemoto Kurokawa
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1992 Volume 65 Issue 4 Pages 965-970

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Abstract

The racemization rates of N-acetyl-(S)-tyrosine, N-acetyl-(S)-phenylalanine, N-acetyl-(R)-2-(4-hydroxyphenyl)glycine [(R)-AcHpg], N-acetyl-(R)-2-phenylglycine, and N-acetyl-(S)-alanine were measured by use of (RS)-α-methylbenzylamine [(RS)-MBA] as a base-catalyst. The first-order rate constant for racemization tended to increase with an increase in the polar substituent constant of the N-acetylamino acid side chain. The racemization appeared to be subject to the inductive effect by the side chain. An asymmetric transformation of (RS)-AcHpg by using (R)-MBA, based on the result of racemization, gave an optically pure salt of (R)-AcHpg with (R)-MBA by successive use of the filtrate as the solvent. Optically pure (R)-2-(4-hydroxyphenyl)glycine [(R)-Hpg] was separated from the salt in 87–90% yield based on the starting (RS)-AcHpg. In addition, the asymmetric transformation of (R)-AcHpg was achieved by using (S)-MBA to give optically pure (S)-Hpg in 80% yield after purification of the salt of (S)-AcHpg with (S)-MBA followed by hydrolysis.

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© 1992 The Chemical Society of Japan
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