Awesome Chemistry Experiments For 2,5-Dichlorobenzooxazole

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Practical synthesis of an enantiomerically pure trans-4,5-disubstituted 2-pyrrolidinone via enzymatic resolution. Preparation of the LTB4 inhibitor BIRZ-227

A practical synthesis of the enantiomerically pure BIRZ-227 (1), a LTB4 inhibitor, has been developed. The key steps include the effective synthesis of the trans-diarylpyrrolidinone (¡À)-8 and the enzymatic resolution of N- acetoxymethyl pyrrolidinone (¡À)-10 by immobilized Lipase Novozym 435. Reduction of pyrrolidinone (+)-8 with borane and subsequent coupling with chlorobenzoxazole 2 furnished BIRZ-227 in high enantiomeric purity (99% ee). The overall process described herein required no chromatographic separation and is amenable to the preparation of multikilogram quantities of the desired drug candidate in a cost-effective manner.

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Reference£º
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem