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Loss of the tert-butyloxycarbonyl (Boc) protecting group under basic conditions

1994; Elsevier BV; Volume: 35; Issue: 30 Linguagem: Inglês

10.1016/s0040-4039(00)73512-x

1873-3581

Timothy P. Curran, Michael P. Pollastri, Susan M. Abelleira, Renee J. Messier, Theresa A. McCollum, Campbell G. Rowe,

Synthesis of Organic Compounds

Reaction of 3, the N-Boc, O-tosyl derivative of phenylalaninol, with base leads to loss of the Boc and tosyl groups and formation of oxazolidinone 9. Similar reactions have also been examined. A mechanism to explain loss of the Boc group under basic reaction conditions is proposed.