Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From silicon reactant having at least one...
Patent
1985-03-15
1986-10-28
Marquis, Melvyn I.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From silicon reactant having at least one...
528 10, 528 39, 252184, 252190, 2523156, 2105021, 2105101, C08G 7726
Patent
active
046199845
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
1. Technical Field
The present invention relates to a new packing for use in resolution, particularly in liquid chromatography for optical resolution of racemic compounds. The packing proposed by the present invention is prepared by reacting a silica gel carrier with a so-called silane treating agent to introduce a spacer part therein and chemically bonding it with an optically active D- or L-group.
2. Background Art
Packings for use in optical resolution, comprising silica gel chemically bonded with optically active proline or hydroxyproline, have a carboxyl group coordination-bonded or ionically bonded with a copper ion as described in G. Gubitz et al. "J. High Resolut. Chromatogr. and Chromatogr. Comm." 2, 145 (1979), K. Sugden et al. "J. Chromatogr." 192, 228 (1980) and V. A. Davankov et al. "Angew. Chem. Int. Ed. Engl." 21, 930 (1982). These packings resolve racemic compounds by taking advantage of a difference in the free energy of the mutual action of the respective antipodes of amino acids with the coordinatable racemic compounds.
In using the conventional packings for resolution, the optically active amino group is bonded with the silane treating agent which acts as the spacer and, therefore, the spacer exerts a significant influence on the resolving capacity and synthetic techniques have been greatly restricted in designing such packings. As described by V. A. Davankov et al. in "Chromatographia" 13, 677 (1980), a process wherein L-hydroxyproline containing a straight-chain alkyl group having 7 to 16 carbon atoms is adsorbed on a reversed phase silica gel column to effect the optical resolution has problems that the groups to be introduced into the amino group are limited to hydrophobic groups and the reactivity and the selection of solvent are difficult. Similar optical resolution packings are disclosed in the specifications of Japanese Patent Laid-Open No. 96062/1983 and corresponding West German Patent Laid-Open No. 3,143,726.
After intensive investigations made for the purpose of further improving the capacities of the known packings, the inventors have found that the resolving power is greatly influenced by the steric bulkiness of the silane treating agent, the distance between the silica gel and the optically active group and the degree of hydrophobicity in said resolution mechanism. The present invention has been completed on the basis of these findings.
DISCLOSURE OF INVENTION The present invention provides a packing for use in
resolution comprising a substance of the following general formula (I): ##STR1## wherein at least one of Y.sup.1, Y.sup.2 and Y.sup.3 represents a silica gel and siloxane bond with the silica gel and the balance represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, a halogen atom, a hydroxy group, an alkoxy group having 1 to 20 carbon atoms or any desired combination of them, and W represents ##STR2## in which X represents a spacer having 1 to 30 carbon atoms, R represents an optically active group of the general formula: ##STR3## where A is a substituted or unsubstituted alkylene group having 2 or 3 carbon atoms and B is a metal thiocarboxylate group, one of X.sup.1 and X.sup.2 represents a hydroxy group and the other represents an optically active group of the formula: ##STR4## where B.sup.1 is a metal carboxylate group, R.sup.1 represents an optically active group of the general formula: ##STR5## where m and n are each 0 or an integer of 1 to 3 and the total of these numbers is up to 3, B.sup.2 is a copper carboxylate or thiocarboxylate, Z is an oxygen atom, a sulfur atom or an amino group and A.sup.1 is a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, an aralkyl group having 7 to 47 carbon atoms or a group having 1 to 40 carbon atoms and a hetero atom, e.g., a group having an ether, amino, thioether, amide, ester, sulfonate or urethane bond, and R.sup.2 represents an optically active gr
REFERENCES:
patent: 4029583 (1977-06-01), Chang et al.
patent: 4322310 (1982-03-01), House
patent: 4324681 (1982-04-01), House
patent: 4455415 (1984-06-01), Panster et al.
patent: 4522724 (1985-06-01), Ramsden
Ichida Akito
Yuki Yoichi
Daicel Chemical Industries Ltd.
Marquis Melvyn I.
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