Process for producing fused imidazole compound, reformatsky...

Details Process for producing fused imidazole compound, reformatsky... Process for producing fused imidazole compound, reformatsky...

2003-01-09

2010-02-16

Stockton, Laura L. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C556S128000

Reexamination Certificate

active

07662974

ABSTRACT:
The present invention provides an industrially advantageous process for producing a steroid C17,20lyase inhibitor represented by the general formula (I):and a Reformatsky reagent in a stable form suitable for the process.In the present invention, a compound represented by the general formula (I) is produced by reducing a specific β-hydroxy ester compound derivative or a salt thereof obtained from a specific carbonyl compound in a Reformatsky reaction in the presence of a metal hydride complex and a metal halide, and then subjecting it to a ring-closing reaction. In the above Reformatsky reaction, it is useful to use a stable solution of a compound represented by the general formula BrZnCH2COOC2H5or a crystal of the compound which is represented by the formula (BrZnCH2COOC2H5.THF)2.

REFERENCES:
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M. Marcel Gaudemar, et al., “Organic Chemistry—On the Preparation, the Structure and the Properties of Reformatsky Complexes”, C.R. Acad. Sc. Paris, (Jan. 10, 1966), t. 262, pp. 213-216—Abstract.
J.J. Chen, et al., “Synthesis and Activity of Conformationally-Constrained Macrocyclic Norstatine-Based Inhibitors of HIV Protease”, Biorganic & Medicinal Chemistry Letters, (1996), pp. 435-438. vol. 6, No. 4.
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J.J. Chen, et al, “Synthesis and Activity of Confomationally-Constrained Macrocyclic Norstatine-Based Inhibitors of HIV Protease”, Bioorganic & Medicinal Chemistry Letters, (1996), 6(4): 435-438; XP-002320038.
K. Soai, et al., “Enantioselective Reformatsky Reaction with Ketones, Asymmetric Synthesis of Beta-(tert-Hydroxy) esters”, J. Chem. Soc. Chem. Commun., (1993), pp. 811-812; XP002396303.
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M. Gaudemar, et al, “Reformatskii Reaction. Structure of a Zinc Derivative of Ethyl Bromoacetate”, Comptas Rendus des Seances de l'Academie des Sciences, Sciences Chimiques, (1968), 267(17): 1053-1056; abstract only; XP-002396307.

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