A New Method of N-Benzhydryl Deprotection in 2-Azetidinone Series

Mathieu Laurent; Marc Belmans; Luc Kemps; Marcel Cérésiat; Jacqueline Marchand-Brynaert

doi:10.1055/s-2003-37653

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Synthesis 2003(4): 0570-0576
DOI: 10.1055/s-2003-37653

PAPER

A New Method of N-Benzhydryl Deprotection in 2-Azetidinone Series

Mathieu Laurent^a, Marc Belmans^b, Luc Kemps^b, Marcel Cérésiat^b, Jacqueline Marchand-Brynaert*^a
^a Université catholique de Louvain, Unité de chimie organique et médicinale, Bâtiment Lavoisier, 1 place Louis Pasteur, 1348 Louvain-la-Neuve, Belgium
Fax: +32(10)474168; e-Mail: marchand@chim.ucl.ac.be;
^b Tessenderlo Chemie s.a./n.v., 130 rue du Trône, 1050 Bruxelles, Belgium

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Publication History

Received 25 November 2002
Publication Date:
07 March 2003 (online)

Abstract
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Abstract

A mild and efficient procedure for the selective cleavage of N-benzhydryl protecting group of β-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 °C for 3 hours. The N-benzhydrol intermediates 6, which could be isolated, were then hydrolyzed with p-TsOH in aqueous acetone to furnish β-lactams 7 and benzophenone quantitatively.

Key words

antibiotics - halogenation - protecting groups - benzhydryl derivatives - stable hemiaminals

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Tinant, B.; Laurent, M.; Marchand-Brynaert, J. Z. Kristallogr. NCS 2002, submitted.