[Justini31]

Reference: Biochemistry (1963) 2, 471.

In this paper, a rearrangement occurs from a hydroxyacetimidic acid (oxime, but one R group is an OH) to give an alpha-amino acid. The reagents used to make this transformation are EtOH/H₂O/NH₄OH, and H₂/PtO₂. I'm familiar with N-based rearrangements, but I've never come across one with an -OH attached to the carbon end of the C=N-OH, nor basic conditions. Can anyone give insight into the mechanism here?

I attached a TIFF picture of the reaction scheme from chemdraw.

Thanks!

[Justini31]

After looking further into the entire reaction scheme, I think the starting material is not a hydroxyacetimidic acid afterall, which makes SO MUCH MORE SENSE now. But if someone thinks the rearrangement is possible, let me know.