Protective groups amines

Alkyl carbamates are generally more stable towards nucleophiles than amides, and are therefore of limited utility as protective groups. Amines lacking other base-sensitive functionalities can, however, be protected as alkyl carbamates. An illustrative example of the use of ethyl carbamate as a protective group is sketched in Figure 10.11 [188]. 

For the reversible immobilization of amines to such linkers, the most frequently used strategy is conversion of the hydroxymethyl linkers into activated carbonic esters (Figure 14.7) [8, 39, 40]. These react with primary and secondary amines or hydrazines to form immobilized carbamates or carbazates analogous to the classical benzyloxycarbonyl protecting group. Amines and hydrazides attached by this strategy to Wang resin can be cleaved with TFA [8, 40]. 

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See also in sourсe #XX -- [ , ]

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