Production methods of epoxytriazole derivative and...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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06884892

ABSTRACT:
An epoxytriazole derivative (V) useful as an intermediate for anti-fungal agents and an intermediate therefor having high quality can be produced economically and efficiently by the following industrial means. A compound of the following formula (I) is reacted with trimethyloxosulfonium salt and the like in the presence of a base to give compound (II), this compound is converted to compound (IV), and this compound is reacted with 1,2,4-triazole in the presence of a base.wherein Ar is a phenyl group optionally substituted by 1 to 3 halogen atom(s) or trifluoromethyl group, R is a hydrogen atom or lower alkyl group, and X is a leaving group.

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Honda et al., “A General Synthetic Method of Chiral 2-Arylalkanoic Esters via Thermal 1,2-Rearrangement,”Bull. Chem. Soc. Jpn., 60(3), 1027-1036 (1987).
Tasaka et al., “Optically Active Antifungal Azoles. I. Synthesis and Antifungal Activity of (2R,3R)-2-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol and Its Stereoisomers,”Chem. Pharm. Bull., 41(6), 1035-1042 (1993).
Saji et al., “Stereoselective Synthesis of Antifungal Agentthreo-2-(2,4-Difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol (SM-8668),”Bull. Chem. Soc. Jpn., 67(5), 1427-1433 (1994).
Tasaka et al., “Optically Active Antifungal Azoles. IV. Synthesis and Antifungal Activity of (2R,3R)-3-Azolyl-2-(substituted phenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanols,”Chem. Pharm. Bull., 43(3), 432-440 (1995).
Gala et al., “Total Chiral Synthesis of Azole Antifungals via α-Hydroxylation of Ketones,”Tetrahedron Letters, 37(45), 8117-8120 (1996).

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