Boc Protected Compounds
Boc Protected Compounds
tert-Butyloxycarbonyl (Boc) is a protecting group often used in the synthesis of organic compounds. Boc is specifically used to protect amine in the solid phase synthesis of peptides (Green, T. W.; Wuts, P. G. M., Protective Groups in Organic Synthesis, Wiley-Interscience: New York, 1999, pp 518-525, 736-739). Cleavage of Boc from amino acids, at the last stage, is carried out with trifluroacetic acid or with hydrochloric acid. Di-tert-butyl dicarbonate (BOC-anhydride) and 4-dimethylaminopyridine (DMAP) are used to prepare Boc protected compounds in the absence of any catalyst. Selective cleavage of the Boc group in the presence of other protecting groups is possible when using AlCl3. Boc protection of nitrogen is done in the synthesis of chiral imines from aldehydes. In the Mori synthesis of (-)-isostrychnine from N-tosylamine, after the reduction of the nitrile to amine, the amine is protected with Boc.
