In 2022,Morrill, Charlotte; Gillespie, James E.; Phipps, Robert J. published an article in Angewandte Chemie, International Edition. The title of the article was 《An Aminative Rearrangement of O-(Arenesulfonyl)hydroxylamines: Facile Access to ortho-Sulfonyl Anilines》.Synthetic Route of C5H11NO3 The author mentioned the following in the article:
The discovery of an aromatic rearrangement reaction of O-(arenesulfonyl)hydroxylamines which lead directly to ortho-aminoarylsulfonic acids and ortho-aminobenzenemethanesulfonic acids through formation of a new C-N bond with excellent levels of regiocontrol for the ortho position(s) over all others was reported. The rearrangement was proceeding through an intermol. mechanism and proposed that the regiocontrol observed was the result of attractive non-covalent interactions occurring during the C-N bond-forming step. Importantly, this method was complementary to classical aniline sulfonation in terms of the variously substituted regioisomers that could be obtained and it was also applicable to O-(benzylsulfonyl) hydroxylamines.N-tert-Butoxycarbonylhydroxylamine(cas: 36016-38-3Synthetic Route of C5H11NO3) was used in this study.
N-tert-Butoxycarbonylhydroxylamine(cas: 36016-38-3) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Synthetic Route of C5H11NO3
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