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Synlett 2010(8): 1287-1288  
DOI: 10.1055/s-0029-1219806
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium Hexafluoro-phosphate (HBTU)

Sushilkumar A. Jadhav*
Department of Chemistry & Industrial Chemistry, Via Dodecaneso 31, Genova 16146, Italy
e-Mail: sushil@chimica.unige.it;
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Publication History

Publication Date:
15 April 2010 (online)

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Introduction

The title compound (HBTU, 1) is a useful condensing agent, which has become in the past decade one of the most popular coupling reagents for in situ activation of peptide synthesis both in solid phase and in solution. [¹-5] The same benzotriazolyl derivative has also been successfully employed for esterifications, as for example in solid-phase nucleotide synthesis. [6] [7] In addition to its high reactivity, HBTU has also been shown to fulfill the very important requirement of minimizing racemization at adjacent sites. Sometimes, hydroxybenzotriazole (HOBt) is used together with HBTU as racemization suppressor. Thus, HBTU effectively performs condensation with high yields and minimal racemization, in simple experimental conditions and within short reaction times.

Figure 1