Abstract
The asymmetric synthesis of monocyclic β-lactams belong to five categories: a) asymmetric induction from the imine component; b) asymmetric induction from the ketene component; c) double stereodifferentiating cycloadditions; d) carbacephem intermediates and e) 2-oxaisocephems and 2-isocephems.[...]
Highlights
Treatment of S- (-)-tyrosine ethyl ester hydrochloride with 2-hydroxybenzaldehyde in the presence of triethylamine in dry benzene afforded Schiff base 1 as a yellow crystal
The reaction mixture was stirred at room temperature for 24 hours
The formation of new product was confirmed by the presence of β-lactam carbonyl group at 1780 cm-1 in its IR spectrum
Summary
Treatment of S- (-)-tyrosine ethyl ester hydrochloride with 2-hydroxybenzaldehyde (salicylaldehyde) in the presence of triethylamine in dry benzene afforded Schiff base 1 as a yellow crystal. To the cold solution of mixture of Schiff base 1 (3.13 g, 10.00 mmol) and phthaloylglycyl chloride (2.37 g, 10.00 mmol) in dry methylene chloride (30 ml/g of phthaloyl), was added slowly triethylamine (1.31 g, 13.00 mmol) in methylene chloride (10 ml/g of the base). The reaction mixture was stirred at room temperature for 24 hours.
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