1-t-Butoxycarbonyl-1,2,4-triazole

[41864-24-8]  · C7H11N3O2  · 1-t-Butoxycarbonyl-1,2,4-triazole  · (MW 169.18)

(a reagent for protection of amines with the t-butoxycarbonyl group1)

Physical Data: mp 40 °C.

Solubility: sol DMF and DMSO.

Form Supplied in: the reagent is commercially available and is supplied as a solid.

Preparative Method: 1-t-butoxycarbonyl-1,2,4-triazole (1) is available commercially, but it can readily be prepared from the reaction of t-butoxycarbonyl azide with 1-trimethylsilyl-1,2,4-triazole or reaction of t-butanol with N,N-carbonyl-di-1,2,4-triazole in high yield.1

Handling, Storage, and Precautions: anhydrous conditions are recommended for reactions, and the reagent is best stored at 0-4 °C.

t-Butoxycarbonylation.

(1) is exceedingly reactive towards amines. Simple amines react with (1) to give the corresponding carbamates in high yields. However, the reaction has been reported to proceed somewhat more slowly with carboxylate salts of amino acids. Nonetheless, yields for the protection of amino acids under these conditions are in the range of 80-92%.1

Related Reagents.

2-(t-Butoxycarbonyloxyimino)-2-phenylacetonitrile; N-(t-Butoxycarbonyloxy)phthalimide; N-(t-Butoxycarbonyloxy)succinimide; t-Butyl Azidoformate; t-Butyl Chloroformate; Di-t-butyl Dicarbonate.


1. Bram, G. TL 1973, 469.

Ioannis Grapsas & Shahriar Mobashery

Wayne State University, Detroit, MI, USA



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