Unknown

Dataset Information

0

Improved Synthesis of a Cyclic Glutamine Analogue Used in Antiviral Agents Targeting 3C and 3CL Proteases Including SARS-CoV-2 Mpro.


ABSTRACT: An intermediate in the synthesis of numerous antiviral protease inhibitors is the glutamine analogue, (3S)-pyrrolid-2-one-3-yl-l-alanine. Preparations of compounds based on this pharmacophore are hindered by the lack of a reliably high yielding synthesis of protected forms of this amino acid. We describe an improved scalable route with readily available reagents and facile purification. This methodology employs γ-allylation of dimethyl N-BocGlu, further Boc N-protection, OsO4-periodate oxidation, O-Me oxime formation, and RaNi-catalyzed hydrogenolysis with concomitant cyclization under basic conditions.

SUBMITTER: Vuong W 

PROVIDER: S-EPMC8425337 | biostudies-literature |

REPOSITORIES: biostudies-literature

Similar Datasets

| S-EPMC8018918 | biostudies-literature
| S-EPMC7409838 | biostudies-literature
| S-EPMC8248761 | biostudies-literature
| S-EPMC7441806 | biostudies-literature
| S-EPMC8178537 | biostudies-literature
| S-EPMC9638714 | biostudies-literature
| S-EPMC10934083 | biostudies-literature
| S-EPMC8506074 | biostudies-literature
| S-EPMC9866112 | biostudies-literature
| S-EPMC7062204 | biostudies-literature