Methods for forming protected organoboronic acids
AssigneeThe Board of Trustees of the University of Illinois
InventorsMartin D. Burke, Graham R. Dick, David M. Knapp, Eric P. Gillis, Jenna A. Klubnick
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Abstract
Described are methods of forming protected boronic acids that provide in a manner that is straightforward, scalable, and cost-effective a wide variety of building blocks, such as building blocks containing complex and/or pharmaceutically important structures, and/or provide simple or complex protected organoboronic acid building blocks. A first method includes reacting an imino-di-carboxylic acid and an organoboronate salt. A second method includes reacting a N-substituted morpholine dione and an organoboronic acid.
Claims18
A method of forming a protected boronic acid, comprising:
- reacting in a reaction mixture
- an imino-di-carboxylic acid, and
- an organoboronate salt represented by formula (I):
- [R1—B(OR2)(OR3)(OR4)]−M+ (I);
- wherein
- R1 is an organic group,
- R2, R3 and R4 independently are selected from the group consisting of an alkyl group and an aryl group, and
- M+ is selected from the group consisting of a metal ion, a metal halide ion and an ammonium ion;
- and
- the reaction mixture further comprises a polar aprotic solvent;
- wherein the reacting comprises maintaining the reaction mixture at a temperature of at least 100° C.;
- and
- thereby forming a protected organoboronic acid represented by formula (III) in the reaction mixture:
- wherein R10, R11, R12, R13 and R14 independently are selected from the group consisting of a hydrogen group and an organic group.
Dependencies are inferred from the claim text.