Di-tert-butyl Dicarbonate (Boc-anhydride, Boc2O)

Debendra K. Mohapatra

doi:10.1055/s-2001-18768

Synlett 2001; 2001(12): 1995-1996
DOI: 10.1055/s-2001-18768

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Di-tert-butyl Dicarbonate (Boc-anhydride, Boc₂O)

Debendra K. Mohapatra^*

^*OCT Division, National Chemical Laboratory, Pune - 411 008, India

Abstract

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The multifarious role of di-tert-butyl dicarbonate (Boc-anhydride, Boc₂O) as protecting group, isocyanating agent, activator of carboxylic acid, lactonisation agent and as a dehydrating agent has been well documented in the records of literature. It is also an efficient tert-butoxycarbonylating agent for alcohols, thiols, amines and carbon nucleophiles. From our group, it has also been exploited as a cyclodehydrating agent for N-acylamino acids forming oxazoles and benzoxazinones and as a novel reagent for an efficient synthesis of dipeptides under mild, non-racemizing conditions. It’s inexpensive, easy to introduce and cleave as a protecting group, gives innocuous by-products t-BuOH and CO₂, and it’s mild, and high yielding reaction procedures all add to its value as a versatile and eco-friendly reagent.

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