Production method of optically active diphenylalanine compounds

Details Production method of optically active diphenylalanine compounds Production method of optically active diphenylalanine compounds

2006-05-10

2008-09-23

Eyler, Yvonne (Department: 1621)

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

Organic compounds

Carboxylic acids and salts thereof

C562S450000, C562S405000, C560S037000

Reexamination Certificate

active

07427688

ABSTRACT:
The present invention provides a production method including reacting a diphenylmethylene halide compound represented by the following formula (1) with a malonic acid diester compound represented by the following formula (2) in an organic solvent selected from N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone and N,N-dimethylformamide, in the presence of a base selected from an alkali metal hydride and an alkali metal t-butoxide to give a diester compound represented by the following formula (3), and then subjecting the diester compound to hydrolysis and decarboxylation to give a diphenylalanine compound represented by the following formula (4).According to the present invention, diphenylalanine compound (4) can be obtained industrially advantageously in a high yield.wherein each symbol is as defined in the specification.

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J.-W. Chang, et al., “An Efficient Synthesis of N-Boc-D-Diphenylalanine From a Chiral Azirdine-2-Carboxylate”, Heterocylces, vol. 57, No. 6, 2002, pp. 1143-1148.
H.G. Chen, et al., “Chiral Synthesis of D- and L-3,3-Diphenylalanine (DIP), Unusual Alpha-Amino Acids for Peptides of Biological Interest”, Tetrahedron Letters, vol. 33, No. 23, 1992, pp. 3293-3296.
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