The Journal of Organic Chemistry

New Methods of Introducing the Carbo-t-butoxy Amino-Protecting Group. Preparation and Use of t-Butyl Cyanoformate and t-Butyl Iminodicarboxylate1

LA Carpino

文献索引：Carpino,L.A. Journal of Organic Chemistry, 1964 , vol. 29, p. 2820 - 2824

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被引用次数: 67

摘要

A new route to the potentially useful carbo-t-butoxylating agent, t-butyl cyanoformate (I), is described which involves treatment of a t-butyl a-alkoxyacetate with N-bromosuccinimide followed by hydrolysis of the intermediate a-bromo ester (IV) and reaction of the resuking glyoxylate solution with hydroxylamine to yield t-butyl oximinoacetate (11). Dehydration of the oxime by means of acetic anhydride and triethylamine gave the cyanoformate (I). As ...