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1-[(1S,2S)-1,2-Bis(2-hydroxyphenyl)-2-pivaloylaminoethylamino]-2,2-dimethyl-1-propanone

Department of Chemistry, Pennsylvania State University-York, 1031 Edgecomb Avenue, York, PA 17403, USA
Molbank 2019, 2019(1), M1054; https://doi.org/10.3390/M1054
Received: 6 March 2019 / Revised: 19 March 2019 / Accepted: 21 March 2019 / Published: 22 March 2019
(This article belongs to the Section Organic Synthesis)
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PDF [318 KB, uploaded 22 March 2019]

Abstract

When 2-[(1S,2S)-1,2-diamino-2(2-hydroxyphenyl)ethyl]phenol (I) was reacted with 2 mole equivalents of trimethyl acetic (pivalic) anhydride in tetrahydrofuran at room temperature, 1-[(1S,2S)-1,2-bis(2-hydroxyphenyl)-2-pivaloylaminoethylamino]-2,2-dimethyl-1-propanone (II) was obtained quantitatively as the only product. The structure of the product was determined using 1H- and 13C-NMR. The COSY spectrum indicated that the single –NH was coupled to the single benzylic proton, –CH. The versality of the transformation could be used to generate additional compounds for use in various research areas. View Full-Text
Keywords: selective pivaloylation; 2-[(1S,2S)-1,2-diamino-2(2-hydroxyphenyl)ethyl]phenol; 1-[(1S,2S)-1,2-bis(2-hydroxyphenyl)-2-pivaloylaminoethylamino]-2,2-dimethyl-1-propanone selective pivaloylation; 2-[(1S,2S)-1,2-diamino-2(2-hydroxyphenyl)ethyl]phenol; 1-[(1S,2S)-1,2-bis(2-hydroxyphenyl)-2-pivaloylaminoethylamino]-2,2-dimethyl-1-propanone
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Lugemwa, F.N. 1-[(1S,2S)-1,2-Bis(2-hydroxyphenyl)-2-pivaloylaminoethylamino]-2,2-dimethyl-1-propanone. Molbank 2019, 2019, M1054.

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