Catalytic Asymmetric Synthesis of the anti-COVID-19 Drug Remdesivir.
Angew Chem Int Ed Engl
; 59(47): 20814-20819, 2020 11 16.
Article
in English
| MEDLINE | ID: covidwho-739123
ABSTRACT
The catalytic asymmetric synthesis of the anti-COVID-19 drug Remdesivir has been realized by the coupling of the P-racemic phosphoryl chloride with protected nucleoside GS441524. The chiral bicyclic imidazole catalyst used is crucial for the dynamic kinetic asymmetric transformation (DyKAT) to proceed smoothly with high reactivity and excellent stereoselectivity (96 % conv., 221 SPRP ). Mechanistic studies showed that this DyKAT is a first-order visual kinetic reaction dependent on the catalyst concentration. The unique chiral bicyclic imidazole skeleton and carbamate substituent of the catalyst are both required for the racemization process, involving the phosphoryl chloride, and subsequent stereodiscriminating step. A 10â
gram scale reaction was also conducted with comparably excellent results, showing its potential for industrial application.
Keywords
Full text:
Available
Collection:
International databases
Database:
MEDLINE
Main subject:
Antiviral Agents
/
Adenosine Monophosphate
/
Alanine
Limits:
Humans
Language:
English
Journal:
Angew Chem Int Ed Engl
Year:
2020
Document Type:
Article
Affiliation country:
Anie.202011527
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