Photocatalyzed process for producing carbapenams and carbapen-2-

Details Photocatalyzed process for producing carbapenams and carbapen-2- Photocatalyzed process for producing carbapenams and carbapen-2-

1981-02-09

1982-09-07

Williams, Howard S.

Chemistry: electrical and wave energy

Processes and products

Processes of treating materials by wave energy

B01J 1912

Patent

active

043482643

ABSTRACT:
Carbapenam-3-carboxylic acids and carbapen-2-em-3-carboxylic acids substituted at the 1-position with an oxo, a hydroxy or an acetoxy group, variously substituted at the 2-position with such groups as methyl, acetoxymethyl, methanesulfonyloxy, alkoxy, alkylthio, aminoalkylthio or amidinoalkylthio and optionally substituted at the 6-position with a hydroxyalkyl group, an acetoxyalkyl group or a conventional penicillin side-chain, pharmaceutically-acceptable salts thereof and various esters thereof wherein the esterifying group is selectively removed in the laboratory, or hydrolyzed under physiological conditions.
These compounds are useful either systemically or topically in the treatment of diseases caused by susceptible microorganisms, as animal feed additives for promotion of growth, or in the preservation of biodegradable materials, or as intermediates to compounds having such antibacterial activity.
Key to the synthesis of these compounds is the light catalyzed rearrangement of 2-diazo-1-oxoceph-3-em-4-carboxylates to 1-oxocarbapen-2-em-3-carboxylates, a newly discovered reaction determined to be of general applicability.

REFERENCES:
patent: 3592751 (1971-07-01), Archer et al.
patent: 4208422 (1980-06-01), Christensen et al.
patent: 4234596 (1980-11-01), Christenson et al.
Kemetani et al., Heterocycles, 12, pp. 1189-1190 (1979).
Onoue et al., Tetrahedron Letters No. 40, pp. 3867-3870 (1979).
Baxter et al., J. Chem. Soc. Chem. Commun. 1979, pp. 236-237 (1979).
Cama and Christensen, J. Am. Chem. Soc., 100, pp. 8006-8007 (1979).
Ratcliffe et al., Tetrahedron Letters 21, pp. 31-34 (1980).

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