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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 9
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Original Articles

A General N-Alkylation Procedure for Ethyl Pyroglutamate

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Pages 1827-1838 | Received 30 Sep 1995, Published online: 21 Aug 2006
 

Abstract

Despite several reported procedures for coupling alkyl halides and 5-oxoproline esters (pyroglutamate derivatives), no general method has been described. The reaction of pyroglutamate with sodium hydride, in anhydrous THF in the presence of the halide, provides this general and practical alkylation method. Alkylation under phase transfer conditions is a useful, but less general, alternative.

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