Issue 57, 2016
From the journal:

Chemical Communications

Direct amidation of unprotected amino acids using B(OCH2CF3)3†

Rachel M. Lanigan,‡a   Valerija Karaluka,‡a   Marco T. Sabatini,‡a   Pavel Starkov, ORCID logo §a   Matthew Badland,b   Lee Boultonc  and  Tom D. Sheppard*a  

* Corresponding authors

a Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon St, London, WC1H 0AJ, UK
E-mail: tom.sheppard@ucl.ac.uk

b Pfizer Global Pharmaceutical Sciences, Discovery Park, Ramsgate Road, Sandwich, Kent, UK

c GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Herts, UK

Abstract

A commercially available borate ester, B(OCH2CF3)3, can be used to achieve protecting-group free direct amidation of α-amino acids with a range of amines in cyclopentyl methyl ether. The method can be applied to the synthesis of medicinally relevant compounds, and can be scaled up to obtain gram quantities of products.

Graphical abstract: Direct amidation of unprotected amino acids using B(OCH2CF3)3

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Article information

DOI
https://doi.org/10.1039/C6CC05147B
Article type
Communication
Submitted
29 Jan 2016
Accepted
22 Jun 2016
First published
22 Jun 2016
This article is Open Access
Creative Commons BY license

Chem. Commun., 2016,52, 8846-8849

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Direct amidation of unprotected amino acids using B(OCH2CF3)3

R. M. Lanigan, V. Karaluka, M. T. Sabatini, P. Starkov, M. Badland, L. Boulton and T. D. Sheppard, Chem. Commun., 2016, 52, 8846 DOI: 10.1039/C6CC05147B

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