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The design of efficient and selective routes to a key 1,4-cis-substituted cyclohexylamide intermediate |
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| Authors: | Christopher Barfoot David T. Davies Ilaria Giordano Graham Jones Michael McGuire Neil Pearson Ravinder Sudini Jeffery Wood |
| Affiliation: | a Antibacterial Discovery Performance Unit, Infectious Diseases CEDD, GlaxoSmithKline, Gunnels Wood Road, Stevenage SG1 2NY, UK b Antibacterial Discovery Performance Unit, Infectious Diseases CEDD, GlaxoSmithKline, Third Avenue, Harlow CM19 5AW, UK c Synthetic Chemistry, GlaxoSmithKline, 709 Swedeland Road, King of Prussia, PA 19406, USA d Antibacterial Discovery Performance Unit, Infectious Diseases CEDD, GlaxoSmithKline, 1250 South Collegeville Road, Collegeville, PA 19426, USA |
| Abstract: | This Letter describes the synthetic challenges in synthesising key 1,4-cis-substituted cyclohexylamide intermediate 1 for our research programme. Five different routes address the major issues of selectivity to afford the cis product in isomerically pure form and in high yield. Major purification issues were also encountered upon scaling some of the routes. The merits of the diverse routes are assessed and the reasoning given for which one was ultimately used for large-scale synthesis of 1. |
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