Process for producing optically active sulfoxide derivative

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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C514S339000, C514S418000, C546S273400, C546S277400, C548S307100, C548S486000

Reexamination Certificate

active

06982275

ABSTRACT:
The present invention relates to a production method of an optically active form of a compound represented by formula (II)wherein ring A is a benzene ring optionally having substituent(s); R1is H, a hydrocarbon group optionally having substituent(s), an acyl group or an acyloxy group; R2, R3and R4are each H, an alkyl group optionally having substituent(s), an alkoxy group optionally having substituent(s) or an amino group optionally having substituent(s); X is N or CH; Y is N or CH; and * shows an asymmetric center, or a salt thereof, which includes reacting a compound represented by the formula (I)wherein each symbol is as defined above, or a salt thereof, with an excess amount of an oxidizing agent in the presence of a catalyst for asymmetric induction, and provides an efficient production method of an optically active sulfoxide derivative in high yield on an industrial large scale by a convenient method, while achieving an extremely high enantiomer excess.

REFERENCES:
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Donnoli, Maria et al. “Catalytic Asymmetric Oxidation of Aryl Sulfides with a Ti/H20/ (R,R)-Diphenylethane-1,2-diol Complex: a Versatile and Highly Enantioselective Oxidation Protocol.” J. Org. Chem. 1998, vol. 63, pp. 9392-9395.
Donnoli et al, Catalytic Asymmetric Oxidation of Aryl Sulfides with a Ti/H2O/(R,R)-Diphenylethane-1,2-diol Complex: a Versatile and Highly Enantioselective Oxidation Protocol. J. Org. Chem. 1998, vol. 63 No. 25, pp. 9392-9395.
Donnoli, Maria et al. “Catalytic Asymmetric Oxidation of Aryl Sulfides with a Ti/H2O/(R,R)-Diphenylethane-1,2-diol Complex,” J. Org. Chem. (1998), vol. 63, pp 9392-9395.
Cotton et al. “Asymmetric Synthesis of Esomeprazole” Tetrahedron:Asymmetry 11: 3819-3825 (2000).
Pitchen, P., et al., An Efficient Asymmetric Oxidation of Sulfides to Sulfoxides,J. Am. Chem. Soc., (1984), vol. 106, No. 26, pp. 8188-8193.

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