Studies on the oxazolidinone ring formation and the resolution of amine intermediates for the preparation of oxazolidinone antibiotics, linezolid

ORGN 757

HoonGyu Park, hungu860@naver.com1, Bo-Jung Kim, gumung12@nate.com1, and Hakwon Kim, hwkim@khu.ac.kr2. (1) Department of Chemistry, Kyung Hee University, Seocheon-dong, Giheung-gu, Gyeonggi-do, Yongin-si, 446-701, South Korea, (2) Department of Chemistry and The Institute of Natural Science, Kyung Hee University, Seocheon-dong, Giheung-gu, Yongin-si, Gyeonggi-do, 446-701, South Korea
In recent years, oxazolidinone compounds have been discovered as a new antibiotic agent for the effective therapy to antibiotic-resistant species. In this work, we have studied the intramolecular cyclization of N-BOC-protected epoxy amine intermediate(1) under the acidic condition to afford oxazolidinone intermediate(2) and also tested the resolution of the amine intermediate(3) with several chiral acids to give a chiral oxazolidinone intermediate(4) for linezolid.