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Issue 44, 2015
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B(OCH2CF3)3-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether

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Abstract

The use of B(OCH2CF3)3 for mediating direct amidation reactions of a wide range of pharmaceutically relevant carboxylic acids and amines is described, including numerous heterocycle-containing examples. An initial screen of solvents for the direct amidation reaction suggested that cyclopentyl methyl ether, a solvent with a very good safety profile suitable for use over a wide temperature range, was an excellent replacement for the previously used solvent acetonitrile. Under these conditions amides could be prepared from 18 of the 21 carboxylic acids and 18 of the 21 amines examined. Further optimisation of one of the low yielding amidation reactions (36% yield) via a design of experiments approach enabled an 84% yield of the amide to be obtained.

Graphical abstract: B(OCH2CF3)3-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether

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Publication details

The article was received on 28 Aug 2015, accepted on 08 Sep 2015 and first published on 14 Sep 2015


Article type: Paper
DOI: 10.1039/C5OB01801C
Citation: Org. Biomol. Chem., 2015,13, 10888-10894
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    B(OCH2CF3)3-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether

    V. Karaluka, R. M. Lanigan, P. M. Murray, M. Badland and T. D. Sheppard, Org. Biomol. Chem., 2015, 13, 10888
    DOI: 10.1039/C5OB01801C

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