Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 22, Issue 3, Pages 273-277Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.7b00381
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Previous methods to prepare a bicyclic N-hydroxyl urea intermediate in the synthesis of the potent beta-lactamase inhibitor relebactam were effective, but deemed unsuitable for long-term use. Therefore, we developed an in situ protection protocol during hydrogenolysis and a robust deprotection/isolation sequence of this unstable intermediate employing a reactive crystallization. During the hydrogenation studies, we discovered a significant rate enhancement of O-benzyl ether hydrogenolysis in the presence of organic amine bases, especially DABCO. The broader utility of the application of organic bases on the hydrogenolysis of a range of O- and N-benzyl-containing substrates was demonstrated.
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