A new method of N-benzhydryl deprotection in 2-azetidinone series
(2003) Synthesis : journal of synthetic organic chemistry — n° 4, p. 570-576 (2003)
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- Abstract
- A mild and efficient procedure for the selective cleavage of N-benzhydryl protecting group of beta-lactams is described. The protected 2-azetidinones 4, precursors of carbapenems, were treated with a stoichiometric amount of N-bromosuccinimide and a catalytic amount of bromine under sun light irradiation in CH2Cl2-H2O mixture at 20 degreesC for 3 hours. The N-benzhydrol intermediates 6, which could be isolated, were then hydrolyzed with p-TsOH in aqueous acetone to furnish beta-lactams 7 and benzophenone quantitatively.
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Laurent, M., Belmans, M., Kemps, L., Cérésiat, M., & Marchand-Brynaert, J. (2003). A new method of N-benzhydryl deprotection in 2-azetidinone series. Synthesis : journal of synthetic organic chemistry, 4, 570-576. https://hdl.handle.net/2078.5/137246 (Original work published 2003)