Question 6: Scientists around the world are conducting more than 300 clinical trials toinvestigate treatments to help patients infected with the novel coronavirus. Early resultsshow that remdesivir, an antiviral drug originally developed by Gilead Sciences to treatEbola, may be a promising treatment for COVID-19. Consider the structure of remdesivir:NHHNHOOHremdesivira) One of the steps in the synthesis of remdesivir involves the protection of a primaryamine prior to the formation of an organolithium reagent, which acts as a carbanion ina subsequent synthetic step. The reagent used to protect the primary amine istrimethylsilyl chloride (TMS-CI), as shown below:NH2TMSTMS1. 2 TMS-CI, THETMS-CI:2. 4 n-BuLi-Si-CIBDraw a multistep arrow-pushing mechanism to show how the primary amine isprotected using TMS-CI. Assume that the CI leaving group acts as the base.(5 points)b) In the next step of the reaction sequence, a reaction with a lactone results in theformation of a following tricyclic product. Note that the TMS protecting group isremoved using acid after the coupling reaction is complete.TMSBno-TMSNH-Bno OBn2. HotBnoBnoOBnBased on the above reaction, what competing reaction could have occurred if theprimary amine was not protected using TMS-CI? (2 points)c) When designing a synthetic scheme, what is more advantageous to try to include: achemoselective reaction or a protecting group strategy? Explain your reasoning.(2 points)
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