Summary
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1.
The resolution of DL-2-bromo-3-methylbutyric acid into its enantiomorphs was effected with the aid of (+)- and (-)-α-methylbenzylamine.
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2.
A study was made of the reaction of L-2-bromo-3-methylbutyric acid with methylamine under various conditions. It was shown that in all cases the formation of L-N-methylvaline was accompanied by considerable racemization.
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3.
A method was developed for the preparation of the optically active N-methylvalines from D- and L-valines by their tosylation, subsequent methylation with methyliodide, and removal of the tosyl group under the action of sodium in liquid ammonia or of hydrogen bromide in glacial acetic acid.
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4.
The resolution of DL-N-(benzyloxycarbonyl)-N-methylvaline and of DL-N-(p-nitrobenzyloxycarbonyl)-N-methylvaline into their enantiomorphs was effected with the aid of D- and L-threo-2-amino-1-p-nitrophenyl-1,3-propanediol.
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Ovchinnikov, Y.A., Ivanov, V.T. & Kiryushkin, A.A. Depsipeptides. Russ Chem Bull 11, 1955–1961 (1962). https://doi.org/10.1007/BF00921354
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DOI: https://doi.org/10.1007/BF00921354