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AssigneeSchering Corporation
InventorsAshit K. Ganguly, Viyyoor M. Girijavallabhan, Patricia Cavender, Olga Sarre, Stuart W. McCombie
Estimating the term…
.beta.-Lactams having a substituted hydroxymethylene group at the position .alpha. to the lactam carbonyl group are prepared by reaction of an .alpha.-halo-.beta.-lactam with zinc or zinc amalgam in an anhydrous aprotic medium to produce an intermediate which in situ reacts with an appropriate aldehyde or ketone. Also described are novel penicillins and cephalosporins having useful antibacterial activity.
The process for preparing and isolating a .beta.-lactam having a substituted hydroxymethylene group at the position .alpha. to the lactam carbonyl group of the following formulae:
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In which the condensed system contains two hetero rings: ortho-condensed systems
Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula: [IMAGE…:…
Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula: [IMAGE…: with…
Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a
Term ended 11 Aug 1998 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
This invention relates to a novel process and to novel compounds produced thereby.
More specifically, this invention relates to a process for preparing .beta.-lactams having a substituted hydroxymethylene group at the position .alpha. to the lactam carbonyl group and to novel derivatives produced thereby.
In particular, this invention relates to a process for preparing penam and cepham derivatives.
The following examples describe in detail the process of the present invention and the compounds produced therefrom. It will be apparent to those skilled in the art that many modifications, both of materials and methods, may be practiced without departing from the spirit and scope of the invention.
A solution of 11.0 g benzyl 6-diazopenicillanate 1.beta.-oxide and 9 g 3-buten-1-ol in 120 ml dichloromethane is stirred with ice-cooling, and 7.5 g N-bromosuccinimide is added in portions over a 5 minute period. After stirring for 18 minutes at room temperature, the solution is washed successively with water, aqueous sodium sulfite and aqueous sodium bicarbonate. After drying over anhydrous magnesium sulfate and removal of the solvents in vacuo, the residue is chromatographed on silica gel by eluting rapidly with benzene followed by 10% ethyl acetate in benzene. The product, benzyl 6.alpha.-(3-buten-1-yloxy)-6.beta.-bromopenicillanate 1.beta.-oxide, is isolated as a yellow oil. This compound is represented by the formula: ##STR33##
A solution of 9.2 g benzyl 6.alpha.-(3-buten-1-yloxy)-6.beta.-bromopenicillanate 1.beta.-oxide in 70 ml dry dimethylformamide is cooled to 5.degree. C. Then, 2.4 ml phosphorus tribromide is added dropwise and the mixture is stirred for 1 hour at room temperature. The mixture is added to ice water and extracted with ethyl ether. The organic phase is separated and washed successively with water, sodium bicarbonate solution and saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvents are removed by evaporation. The crude product is chromatographed rapidly on 150 g silica gel using 1:1 dichloromethane-hexane as the eluant, affording benzyl 6.beta.-bromo-6.alpha.-(3-buten-1-yloxy)penicillanate, as a yellow oil, and having the following formula: ##STR34##