Laurent, Mathieu
[UCL]
Belmans, M
Kemps, L
Cérésiat, Marcel
Marchand-Brynaert, Jacqueline
[UCL]
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.
Bibliographic reference |
Laurent, Mathieu ; Belmans, M ; Kemps, L ; Cérésiat, Marcel ; Marchand-Brynaert, Jacqueline. A new method of N-benzhydryl deprotection in 2-azetidinone series. In: Synthesis : journal of synthetic organic chemistry, , no. 4, p. 570-576 (2003) |
Permanent URL |
http://hdl.handle.net/2078.1/41132 |