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A new synthesis of chiral oxazolidinones from the amino acid L-serine

Authors: Nogueira, T.C.M.; Pinheiro, A.C.; Kaiser, C.R.; Wardell, J.L.; Wardell, S.M.S.V.; De Souza, M.V.N.


Abstract

Cyclization of the (4S)-PhCH2OCONHCH(CH2OH)CONHN=CH-aryl, obtained in 4 steps from L-serine, on treatment with MeI and potassium carbonate, generates the chiral oxazolidinones, (4S)-N’-[(E)-(phenyl)methylidene]-Nmethyl- 2-oxo-1,3-oxazolidine-4-carbohydrazides. Overall the formation of the (4S)-N’-[(E)-(phenyl)methylidene]-Nmethyl- 2-oxo-1,3-oxazolidine-4-carbohydrazides from L-serine occurs with retention of configuration, as confirmed by Xray crystallography. In contrast, the reaction of the N-Boc analogues, (4S)-t-BuOCONHCH(CH2OH)CONHN=CH-aryl, on treatment with MeI / K2CO3, simply leads to N-methylation without cyclization and without loss of the Boc protecting group to give (4S)-t-BuOCONMeCH(CH2OH)CONHN=CH-aryl. The difference between the Boc and Cbz derivatives is striking and is probably linked to the greater bulk of the Boc group blocking the intramolecular acyl transfer.

Keywords: L-serine, N-Boc group, N-Cbz group, oxazolidinones, tuberculosis, X-ray crystallography. Document Type: Research Article DOI: http://dx.doi.org/10.2174/15701786113109990028 Publication date: 1 de Janeiro de 2013

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