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

Rachel M Lanigan; Valerija Karaluka; Marco T Sabatini; Pavel Starkov; Matthew Badland; Lee Boulton; Tom D Sheppard

doi:10.1039/c6cc05147b

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

Chem Commun (Camb). 2016 Jul 7;52(57):8846-9. doi: 10.1039/c6cc05147b.

Authors

Rachel M Lanigan¹, Valerija Karaluka¹, Marco T Sabatini¹, Pavel Starkov¹, Matthew Badland², Lee Boulton³, Tom D Sheppard¹

Affiliations

¹ Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon St, London, WC1H 0AJ, UK. tom.sheppard@ucl.ac.uk.
² Pfizer Global Pharmaceutical Sciences, Discovery Park, Ramsgate Road, Sandwich, Kent CT13 9NJ, UK.
³ GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Herts SG1 2NY, UK.

PMID: 27346362
DOI: 10.1039/c6cc05147b

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.