Deprotection by Acidolysis ferf-Butyl-Based Protectors

6 DEPROTECTION BY ACIDOLYSIS ferf-BUTYL-BASED PROTECTORS 

FIGURE 3.6 Deprotection of functional groups by acidolysis. Protonation followed by carbocation formation during the removal of ferf-butyl-based protectors by hydrogen chloride.8 One mechanism is involved in generating the ferf-butyl cation, which is the precursor of two other molecules. 

GW Anderson, AC McGregor. t-Butyloxycarbonylamino acids and their use in peptide synthesis. J Am Chem Soc 79, 6180, 1957. 

R Schwyzer, W Rittel, H Kappeler, B Iselin. Synthesis of a nonadecapeptide with higher corticotropic activity, pert-butyl removal) Angew Chem 72, 915, 1960. 

RE Reid. Solid phase peptide synthesis. A study on the effect of trifluoroacetic acid concentration on the removal of the tert-butyloxycarbonyl protecting group. J Org Chem 41, 1027, 1976. 

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