Resins having vinyl ether linker for the solid phase organic synthesis
AssigneeKorean Research Institute of Chemical Technology
InventorsSungEun Yoo, YoungDae Gong, JinSoo Seo
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Abstract
The present invention relates to a resin having a vinyl ether linker and more particularly, to a resin having a vinyl ether linker expressed by formula (I), useful for the synthesis of compounds having hetero atoms such as alcohol, thiol, imidazole, triazole and tetrazole by employing combinatorial chemical synthesis on solid supports.
Claims13
A resin having vinyl ether linker expressed by formula (1) useful as a solid-phase support in combinatorial chemical synthesis,
- wherein {circle around (P)} is polystyrene-divinylbenzene;
- and n is an integer of 1 to 5.
A process for preparing a resin having vinyl ether linker of formula (1) comprising:
- (a) a reduction of methyl(4-hydroxybenzyl)ester of formula (2) to 4-hydroxyphenethyl alcohol of formula (3);
- (b) a reaction of the obtained 4-hydroxyphenethyl alcohol of formula (3) with ethylvinyl ether of formula (4) to produce 4-(2-vinyloxyethyl)phenol of formula (5);
- and
- (c) a reaction of the obtained 4-(2-vinyloxyethyl)phenol of formula (5) with Merrifield resin of formula (6) to produce the resin having vinyl ether linker expressed by formula (1),
- wherein {circle around (P)} is polystyrene-divinylbenzene;
- and n is an integer of 1 to 5.
An organic synthesis on solid-phase support, comprising introducing a hetero atom-containing compound of formula (7) using a resin having vinyl ether linker of formula (1) as a solid support, performing multi-step reaction, and cleaving the hetero atom-containing compound of formula (7) from the solid support,
- HY—(CH2)m—X (7)
- wherein {circle around (P)} is polystyrene-divinylbenzene;
- Y is O or NH;
- X is H, OH, SH, a halogen atom, phenyl, phenyl or biphenyl substituted with halogen atom(s), or
- formed by bonding another hetero atom (X′) with Y, where Y and X′ are independently from 1 to 5 hetero atoms and the bonding is chosen from C1-C4 alkylenes and alkenyls;
- and
- M is an integer of 1 to 4.
A resin having vinyl ether linker expressed by formula (1) useful as a solid-phase support in combinatorial chemical synthesis,
- wherein {circle around (P)} is a resin;
- and n is an integer of 1 to 5.
An organic synthesis on solid-phase support, comprising introducing a hetero atom-containing compound of formula (7) using a resin having vinyl ether linker of formula (1) as a solid support, performing a multi-step reaction, and cleaving the hetero atom-containing compound of formula (7) from the solid support, HY—(CH2)m—X (7)
- wherein {circle around (P)} is resin;
- Y is O or NH;
- X is H, OH, SH, a halogen atom, phenyl, phenyl or biphenyl substituted with halogen atom(s), or
- formed by bonding another hetero atom (X′) with Y, where Y and X′ are independently from 1 to 5 hetero atoms and the bonding is chosen from C1-C4 alkylenes and alkenyls;
- and
- M is an integer of 1 to 4.
Dependencies are inferred from the claim text.