SYNTHESIS AND STRUCTURAL MODIFICATION OF <i>tert</i>-BUTYL ESTER OF 7α-CHLORO-2-(N,N-DIMETHYLAMINOMETHYLENE)-3-METHYL-1,1-DIOXOCEPH-3-EM-4-CARBOXYLIC ACID

Abstract

The reaction of tert-butyl 7α-chloro- and 7-β-chloro-7α-isopropoxy-3-methyl-1,1-dioxoceph-3-em-4-carboxylates with the Vilsmeier reagent was  carried out with introduction of N,N-dimethyl-aminomethylene group at position 2 in the E- and Z-isomeric forms. Prolonged treatment of tert-butyl 7α-chloro-3-methyl-2-(N,N-dimethylaminomethylene)-1,1-dioxoceph-3-em-4-carboxylate with hydroxyl-amine hydrochloride in acetonitrile at 40-50°C gave tert-butyl 10(S)-chloro-6-methyl-5-oxa-1,1,9-trioxo-1-thia-4,8-diazatricyclo[7,2,0,02,6]undecane-7(R)-carboxylate which isomerized into 1-tert-butoxycarbonylmethyl-3α-chloro-4-(5-methylisoxazole-4-sulfonyl)azetidin-2-one. In the case of tert-butyl 7β-chloro-7α-isopropoxy-3-methyl-2-(N,N-dimethylaminomethylen)-1,1-dioxoceph-3-em-4-carboxy-
late the analogous reaction gave tert-butyl 10β-chloro-(2S,6S,7S,10R,11R)-10α-isopropoxy-6-methyl-5-oxa-1,1,9-trioxo-1-thia-4,8-diazatricyclo[7,2,0,02,6]undecane-7(R)-carboxylate, the struc-ture of which was determined by 2D-NOESY two-dimensional spectroscopy. The compounds synthesized showed weak or no cytotoxic activity with respect to monolayers of cancer cells in vitro. 

How to Cite
Vorona, M.; Potoročina, I.; Veinberg, G.; Shestakova, I.; Kanepe, I.; Petrova, M.; Liepinsh, E.; Lukevics, E.  Chem. Heterocycl. Compd. 2007, 43, 646. [Khim. Geterotsikl. Soedin. 2007, 769.]

For this article in the English edition see DOI 10.1007/s10593-007-0101-2