Process of producing optically active propionic acid ester deriv

Details Process of producing optically active propionic acid ester deriv Process of producing optically active propionic acid ester deriv

1990-07-25

1993-11-02

Higel, Floyd D.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544354, 546268, 546283, 548170, 549501, C07D21355, C07D21379, A01N 4340

Patent

active

052585212

ABSTRACT:
Processes for producing optically active ester derivatives are disclosed. According to the present invention an optically active aryloxyphenoxy propionate derivative is produced by reacting a chlorinated heterocyclic aromatic compound with (2R)-2-(4-hydroxyphenoxy)propionic acid tetrahydrofurfuryl ester in an anhydrous solvent in the presence of a base. According to the present invention, an optically active propionate derivative of the formula [I] ##STR1## (wherein R represents hydrogen or 3-chloro-5-trifluoromethyl-2-pyridyl group) is produced by reacting a corresponding optically active methyl propionate derivative with tetrahydrofurfuryl alcohol, or by reacting a corresponding optically active propionic acid derivative with tetrahydrofurfuryl alcohol, or by reacting (2S)-tetrahydrofurfuryl 2-chloropropionate with a corresponding phenol derivative in specific conditions.

REFERENCES:
patent: 3773773 (1973-11-01), Bossert
patent: 4532328 (1985-07-01), Kleschick
Gilman, et al., Organic Synthesis, 2nd Ed., John Wiley & Sons, New York, pp. 296-299, pp. 434-437 (1972).
Hoening, et al., Organic Synthesis, Collective vol. 3, John Wiley & Sons, New York, pp. 46-49 & 140-141, 146-149, 200-205, 418-421, (1965).
Baumgarten et al., Organic Synthesis, Collective vol. 5, John Wiley and Sons, New York, pp. 250-255, (1960).
Pine, et al., Organic Chemistry, 4th Ed., McGraw-Hill, London, pp. 272-275, 376-379, (1957).
Morrison & Boyd, Organic Chemistry, 5th Edition, Allyn & Bacon, Inc., Boston, 1987, pp. 703, 875, 830.

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