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tert-Butyloxycarbonyl protecting group. The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group [1] (BOC group) is an acid-labile protecting group used in organic synthesis. The BOC group can be added to amines under aqueous conditions using di-tert-butyl dicarbonate in the presence of a base such as sodium hydroxide:
Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis. [1] Since this compound can be regarded formally as the acid anhydride derived from a tert-butoxycarbonyl (Boc) group, it is commonly referred to as Boc anhydride. This pyrocarbonate reacts with amines to give N-tert-butoxycarbonyl or so-called Boc
tert-Butyloxycarbonyl (Boc) group — Removed by concentrated strong acid (such as HCl [52] or CF 3 COOH [53]), or by heating to >80 °C. Common in solid phase peptide synthesis . 9-Fluorenylmethyloxycarbonyl ( Fmoc ) group — Removed by base, such as 20–50 % piperidine in dimethylformamide (DMF) [ 54 ] or N -Methyl-2-pyrrolidone , [ 55 ] or ...
The effect of the tert-butyl group on the progress of a chemical reaction is called the Thorpe–Ingold effect illustrated in the Diels-Alder reaction below. Compared to a hydrogen substituent, the tert-butyl substituent accelerates the reaction rate by a factor of 240. [2] tert-Butyl effect. The tert-butyl effect is an example of steric hindrance.
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