Resolution of 3-(4-methoxyphenyl)glycidic acid with in situ conv

Details Resolution of 3-(4-methoxyphenyl)glycidic acid with in situ conv Resolution of 3-(4-methoxyphenyl)glycidic acid with in situ conv

1988-05-18

1989-12-05

Hollrah, Glennon H.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30318

Patent

active

048853755

ABSTRACT:
Optically active 3-(4-methoxyphenyl)glycidic acid alkyl esters of high enantiomeric purity can be prepared through optical resolution of a racemic or optically enriched sample of a 3-(4-methoxyphenyl) glycidic acid. The alkali metal salt of the acid, generated in situ by hydrolysis of the corresponding alkyl ester with an alkali metal hydroxide is contacted with a suitable resolving agent such as an optically pure amine to form the corresponding diastereomeric salts. The desired diastereomeric salt is separated from the mixture and transformed to an alkali metal salt, which optionally without isolation is converted into the desired alkyl ester of high enantiomeric purity.

REFERENCES:
patent: 4520203 (1985-05-01), Abraham et al.
Roberts et al., "An Introduction to Modern Experimental Organic Chemistry, Second Edition," Holt, Rinehart and Winston, Inc., New York, NY, (1974), pp. 7-11.
Rudy, C. J., M.A., Thesis, Western Michigan University, Kalamazoo, MI (1985), pp. 56-58.
J. March, "Advanced Organic Chemistry," 2nd ed., pp. 367-368 (1977).
J. Grundy, et al. Tetrahedron Letters (1972), "Esterification of Sterically Hindered Carboxylic Acids Using Dimethyl Sulphate," pp. 757-758.

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