Development of an Effective Scalable Enantioselective Synthesis of the HIV-1 Entry Inhibitor BNM-III-170 as the Bis-trifluoroacetate Salt | Zendy

Junhua Chen | Zendy; Jun Park | Zendy; Sharon Kirk | Zendy; Hung-Ching Chen | Zendy; Xiangqin Li | Zendy; Daniel J. Lippincott | Zendy; Bruno Melillo | Zendy; Amos B. Smith | Zendy

Open Access

Development of an Effective Scalable Enantioselective Synthesis of the HIV-1 Entry Inhibitor BNM-III-170 as the Bis-trifluoroacetate Salt

Author(s) -

Junhua Chen,

Jun Park,

Sharon Kirk,

Hung-Ching Chen,

Xiangqin Li,

Daniel J. Lippincott,

Bruno Melillo,

Amos B. Smith

Publication year - 2019

Publication title -

organic process research and development

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.904

H-Index - 109

eISSN - 1520-586X

pISSN - 1083-6160

DOI - 10.1021/acs.oprd.9b00353

Subject(s) - enantioselective synthesis , human immunodeficiency virus (hiv) , salt (chemistry) , chemistry , combinatorial chemistry , stereochemistry , organic chemistry , virology , medicine , catalysis

We report here the development and optimization of a process synthesis for the HIV-1 entry inhibitor BNM-III-170 bis-TFA salt ( 1 ). The synthesis features a dynamic-kinetic resolution (DKR) to establish the initial stereogenicity. By taking advantage of significant sequence modifications of our first generation synthesis, inconjunction 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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