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Mechanistic insight into oxidized N,N-dimethylacetamide as a source of formaldehyde related derivatives†
Daniel Zewge,Xiaodong Bu,Huaming Sheng,Yizhou Liu,Zhu Liu,Brett Harman,Mikhail Reibarkh,Xiaoyi Gong
Reaction Chemistry & Engineering Pub Date : 02/06/2018 00:00:00 , DOI:10.1039/C7RE00199A
Abstract

A hemiaminal derivative identified during preparation of the penultimate of ceftolozane 1, mandated a thorough investigation of the source of the impurity. N,N-Dimethylacetamide (DMAc) subjected to oxidation was found to be the culprit generating oxidized products that serve as sources of the hemiaminal derivative. Identification of DMAc as a source of formaldehyde derivatives and the mechanism of DMAc oxidation are elaborated.

Graphical abstract: Mechanistic insight into oxidized N,N-dimethylacetamide as a source of formaldehyde related derivatives
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