Atazanavir fragment: spot the fabricated intermediate

Single question

Two-step BMS-style route to the atazanavir hydroxyethylhydrazide. An N-Boc protected amino epoxide is opened with a pyridylbenzyl methoxycarbonyl hydrazide. Check the intermediate after the epoxide opens.

Epoxide aminolysis regiochemistry

Hydroxyethylhydrazide isostere construction

Recognizing impossible quaternary-nitrogen adducts

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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