Synthesis and Crystal Structure of an (N-Protected amino)-β-lactam Derivative of 1,5-Benzothiazepine

1 INTRODUCTION 1,5-Benzothiazepines are a kind of compounds which have important biological activitives1, 2]. Cycloaddition reactions of their active C=N bond with ketene permit the construction of new -lactam ring. The -lactam moiety is the main part of the antibiotics such as penicillins. So the product of this reaction possesses two active centers and can be beneficial to pharmaceutical research. In this paper we have achieved the asymmetric ketene-imine cycloadditions employing the…

Synthesis and Crystal Structure of an (N-Protected amino)- β-lactam Derivative of 1,5-Benzothiazepine

The title compound α-(N-protected amino)-β-lactam (C36H33N2O5ClS), derivative of 1,5-benzothiazepine, was prepared by the reaction of 1,5-benzothiazepine 1 with (4R)- phenyloxazolidylacetyl chloride and characteized by X-ray diffraction analysis. The title compound crystallizes in orthorhombic system, space group P212121 with a=12.293(2), b=26.026(5), c=10.146(2)A, V=3246.1A3, Z=4, Dc=1.312g/cm3, Mr=641.15, F(000)=1344, μ= -0.228 mm-1. The final R=0.0597 and wR=0.1165 for 3226 observed reflections with I ≥ 2σ(I). The crystal structure shows that the 4-phenyloxazolidyl and phenyl attached to C(8) and C(9) are in cis positions, and no trans product was discovered. So the cyclization to β-lactam is stereospecific.