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METHOD OF OBTAINING OPTICALLY ACTIVE ALPHA-ARYLALKINIC ACID OR ITS PHARMACEUTICALLY ACCEPTABLE SODIUM SALT, OR ITS C1-C4 ALKYL OR C1-C4HYDROXYALKYL ESTER
METHOD OF OBTAINING OPTICALLY ACTIVE ALPHA-ARYLALKINIC ACID OR ITS PHARMACEUTICALLY ACCEPTABLE SODIUM SALT, OR ITS C1-C4 ALKYL OR C1-C4HYDROXYALKYL ESTER
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机译:获得光学活性的α-芳基炔酸或其药学上可接受的钠盐或其C1-C4烷基或C1-C4羟烷基酯的方法
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摘要
Pharmaceutically useful optically active alpha -arylalkanoic acids of the formula CHEM where Ar is aryl and R1 is alkyl or cycloalkyl or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting a reagent of the formula Ar-MX, (Ar) 2M or ArM' where M is Cd, Cu(II), Mn(II), Mg or Zn, and M' is Cu(I) or Li, and X is halogen, with an optically active compound of the formula CHEM where Z is a leaving group and Y is halogen, acyloxy or CHEM where R' and R'' are alkyl, aryl or with N are a heterocyclic group, to form the optically active ketone of the formula CHEM which is ketalized and rearranged to said acid, ester, ortho ester or amide. Alternatively, said ketone is reduced to the corresponding alkanol, which is rearranged to the alpha -arylalkanal. The alkanal so produced is converted to said acid by conventional methods.
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