Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 23, Issue 11, Pages 2464-2469Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.9b00353
Keywords
CD4-mimetic; HIV-1 entry inhibitor; dynamic-kinetic resolution; guanidine formation; aminolysis; Gabriel amine synthesis
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Funding
- National Institutes of Health [P01 NIH/NIGMS GM56550/AI150471, RO1 AJ134494, TaPHIR R21 AI129017-01]
- GILEAD, HIV Cure Program
- amfAR, The Foundation for AIDS Research [109343-59-RGRL]
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We report here the development and optimization of a process synthesis for the human immunodeficiency virus-1 entry inhibitor BNM-III-170 bis-trifluoroacetate salt (1). The synthesis features a dynamic-kinetic resolution to establish the initial stereogenicity. By taking advantage of significant sequence modifications of our first-generation synthesis, in conjunction with the low solubility of late-stage intermediates, the overall efficiency of the synthesis has been significantly improved, now to proceed in an overall yield of 9.64% for the 16 steps, requiring only a single chromatographic separation.
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