Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Reexamination Certificate
2001-10-29
2004-08-24
McKane, Joseph K. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
Reexamination Certificate
active
06781009
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a method for producing 4-cyano-3-oxyobutanoate and a process for producing 4-cyano-3-hydroxybutanoate, which is a useful intermediate compound for the production of pharmaceuticals (for example, JP-A-5-331128).
BACKGROUND OF INVENTION
There has been disclosed a method for producing Ethyl 4-cyano-3-oxobutanoate by reacting ethyl 4-bromo-3-oxobutanoate with sodium hydride and reacting the resulting mixture with a cyanide ion in J. Chem. Soc. Chem. Comm. p932-933 (1977).
However, this method was not always satisfactory in that it requires tedious procedures as described above.
SUMMARY OF THE INVENTION
According to the present invention, 4-cyano-3-oxobutanoate can be readily obtained in an industrially improved process, and 4-cyano-3-hydroxybutanoate can also be readily obtained from 4-cyano-3-oxobutanoate.
The present invention provides:
1. a process for producing 4-cyano-3-oxobutanoate of formula (1):
wherein R denotes a C1-C8 alkyl group, which comprises reacting a 4-halo-3-oxobutanoate compound of formula (2):
wherein X and R are defined as described above, with an alkali metal cyanide in methanol;
2. 4-cyano-3-oxobutanoate of formula (1):
wherein R denotes a C1-C8 alkyl group, with the proviso that R is not an ethyl group; and
3. a process for producing 4-cyano-3-hydroxybutanoate of formula (3):
wherein R denotes a C1-C8 alkyl group, which comprises reacting 4-cyano-3-oxobutanoate of formula (1):
with an enzyme capable of converting 4-cyano-3-oxobutanoate of formula (1) to 4-cyano-3-hydroxybutanoate of formula (3), which enzyme has:
a) an amino acid sequence represented by SEQ ID NO:1, or
b) an amino acid sequence wherein one to several amino acids in the amino acid sequence represented by SEQ ID NO:1 are deleted, substituted or added (the enzyme is referred to as “the present enzyme” hereinafter).
REFERENCES:
patent: 0 573 184 (1993-12-01), None
Kellogg et al. Org. Chem. (1980), 45, 2854-2861.*
Troostwijk & Kellogg, “Method for the Synthesis of 4-Substituted Acetoacetates”, J.C.S. Chem. Comm., 1997, (Dept. Of Organic Chemistry, Univ. of Groningen, Nijenborgh, Groningen, The Netherlands), pp. 932-933.
Itoh et al., “Production of Chiral Alcohols By Enantioselective Reduction With NADH-Dependent Phenylacetaldehyde Reductase From Corynebacterium Strain, ST-10”, Journal of Molecular Catalysts B: Enzymatic 6 (1999) pp. 41-50.
Itho et al., “Purification and Characterization of Phenylacetaldehyde Reductase From A Styrene-Assimilating Corybacterium Strain, ST-10”, Dept. of Applied Chemistry & Biotechnology, Faculty of Engineering, Fukui Univ., Japan, Applied & Environmental Microbiology, Oct. 1997, vol. 63, No. 10, pp. 3783-3787.
Wang et al., “Cloning, Sequence Analysis, and Expression inEscherichia Coliof the Gene Encoding Phenylacetaldehyde Reductase From Styrene-Assimilating Corynebacterium Sp. Strain ST-10”, Applied Microbiology Biotechnology (1999) 52: 386-392.
Anderson Rebecca
Fitch Even Tabin & Flannery
McKane Joseph K.
Sumitomo Chemical Company Limited
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