Method of purifying organic compounds using an enantioselective

Details Method of purifying organic compounds using an enantioselective Method of purifying organic compounds using an enantioselective

1994-08-26

1996-11-05

Shah, Mukund J.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540460, 560 18, 560 25, C07D48718, C07D51318, C07D49818, C07B 5700

Patent

active

055719112

ABSTRACT:
The present invention relates to a composition having the general formula: ##STR1## wherein each of A, B, C, X, Y, and Z is independently O, NH, N(CH.sub.2).sub.m CH.sub.3, N(C.dbd.O) (CH.sub.2).sub.m CH.sub.3, CH.sub.2, S, or Se; each of R.sub.1, R.sub.2, and R.sub.3 is independently phenyl, 4-hydroxyphenyl, pyridyl, pyrrolyl, indolyl, naphthyl, thiophenyl, (C.dbd.O) (CH.sub.2).sub.p CH.sub.3, NH(C.dbd.O) (CH.sub.2).sub.p CH.sub.3, OH, COOH, NH.sub.2, or SH; and m, n, and p are integers between 0 and 5. The composition is a chiral receptor molecule useful for the purification of enantiomers of derivatives of amino acids and of compounds able to form hydrogen bonds. The preparation of the composition involves coupling a trifunctional aromatic molecule with three protected chiral molecules at the three aromatic groups, cleaving protecting groups, and joining adjacent chiral groups by multiple lactamizations. The receptor may be used in a form either bound to a solid support or dissolved in an immiscible phase to effect convenient purification of enantiomers or other compounds of interest.

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