Process for the stereospecific preparation of 5-(1-hydroxy-2-ure

Details Process for the stereospecific preparation of 5-(1-hydroxy-2-ure Process for the stereospecific preparation of 5-(1-hydroxy-2-ure

1994-09-15

1996-03-12

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D31906

Patent

active

054987326

ABSTRACT:
The invention relates to a process for the preparation of 5-(1-hydroxy-2-urethanethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives, which are precursors of chiral tetramic acid derivatives.
According to this process, an N-urethane-protected .alpha.-amino acid N-carboxy-anhydride is reacted with Meldrum's acid in an inert organic solvent medium in the presence of a tertiary amine.
This process makes it possible to conserve the chirality of the starting material and in particular to simplify the synthesis of 4-amino-3-hydroxy acids and the derivatives thereof via the tetramic acid route.

REFERENCES:
Jiang et al, "Comparative Study of Selected Reagents for Carboxyl Activation", Tetrahedron Letters, vol. 34, No. 42, Aug. 1993, pp. 6705-6708.
Wuts et al., Synthesis, 1989, 951.
Poncet, et al., J. Chem. Soc. Perkin, Trans. 1, 1990, 611.
Fuller, et al., J. Chem. Soc. vol. 112, No. 20, 1990, 7414-7416.
J. Maibaum, et al., Synthesis of The Novel Py--(Bezylozymethyl)--Protected Histidine Analogue of Statine, Journal Journal of Medicinal Chemistry, vol. 32, No. 7, 1989 1571-1576.
P. Jouin, et al., Stereospecific Synthesis of N-protected Statine and Its Analogues Via Chiral Tetramic Acid, Journal of The Chemical Society, Perkin Trnsactions 1, No. 1, 1987, 1177-1182.

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