Preparation of quinic acid derivatives

Details Preparation of quinic acid derivatives Preparation of quinic acid derivatives

1993-07-21

1995-03-28

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

562508, C07D30700

Patent

active

054018587

ABSTRACT:
3- or 4-mono-, 1,3- or 1,4- or even 3,4-disubstituted derivatives of quinic acid are produced by reaction of a hydroxycinnamic acid derivative, of which the phenol group(s) is/are protected with a quinic acid derivative, to form an ester and the different reactivities of the OH functions in the 3 and 4 positions are used to carry out the esterification selectively under low temperature conditions, after which the protective groups are cleaved under controlled acidity and temperature conditions. These conditions avoid any degradation or isomerization. The process enables new quinides to be obtained in high yields.

REFERENCES:
patent: 3855297 (1974-12-01), Diana et al.
patent: 4818767 (1989-04-01), Rossigual
patent: 4940803 (1990-07-01), Mills et al.
Ichikawa et al. CA 116 (23) 2360952 1992.
Haslam, et al., "Synthesis and Properties of Some Hydroxycinnamoyl Esters of Quinic Acid," J. Chem. Soc., pp. 2137-2146 (1964).
Wynne, et al., Chemical Abstracts, vol. 106, No. 9, No. 64477A (1986).
Ichikawa et al., Chemical Abstracts, vol. 116 No. 23 No. 2360952 (1992).

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