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The following is a snapshot of the synthesis of ammosamide B from Synarchive:

synthesis of ammosamide B

In the final step $\ce{Mg3N2}$ is used to convert esters to amides or amides to amines. What is the mechanism of this process? How does the $\ce{N3-}$ get converted to $\ce{H2O}?$

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    $\begingroup$ Your last phrase is cryptic, as I see no H2O here. $\endgroup$ Sep 12 at 12:38
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$\ce{Mg3N2}$ is magnesium nitride. It reacts with $\ce{MeOH}$ to generate magnesium methoxide and ammonia according to online report by Buske [1]. The $\ce{NH3}$ thus generated is acting as nucleophile to react with the methyl ester to give the primary amide. It also removes two trifluoracetamide groups (or the $\ce{MeO-}$ does) to reveal the amino groups.

Quite why the authors have chosen to use this over more conventional sources of $\ce{NH3}/\ce{MeOH}$ (which is commercially available) is for them to explain.

Reference

  1. Gary Buske. Chemical Safety: $\ce{Mg3N2}$ Hazard. Chemical & Engineering News 2009, 87 (28).
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