Chlorination of the cephem dihydrothiazine ring. Factors influencing C-2 substitution vs. degradation to isothiazoles1

WH Koster, JE Dolfini, B Toeplitz…

Index: Koster,W.H. et al. Journal of Organic Chemistry, 1978 , vol. 43, p. 79 - 82

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Citation Number: 7

Abstract

Results A solution (of la, containing 1 equiv of NCS in deuteriochloroform, was monitored by NMR. Within 15 min the simultaneous disappearance of the NCS singlet (6 2.94) and the AB quartet of the cephem C-2 protons (6 3.43) was observed. The formation of an unstable C-2 substituted A3-cephem, presumed to be the 2-chloro derivative 4a, was indicated by the appearance of the resonances shown in Table 1.5 Simultaneously, a non-p-lactam ...