3-Hydroxy and 3-acetoxy-6-triphenyl-methylaminopenams

Details 3-Hydroxy and 3-acetoxy-6-triphenyl-methylaminopenams 3-Hydroxy and 3-acetoxy-6-triphenyl-methylaminopenams

1976-10-29

1977-07-19

Schwartz, Gerald A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602391, C07C49978

Patent

active

040368467

ABSTRACT:
The present invention discloses novel 6-acylamino-2,2-dimethyl-3-phosphonopenams and certain lower alkyl esters thereof possessing antibacterial activity, methods for their production, and intermediates therefor; the production comprises the steps of reacting 6-triphenylmethylamino-2,2-dimethylpenam-3-carboxylic acid with lead tetraacetate to form the corresponding 3-acetoxy compound, the latter is converted to .alpha.-triphenylmethylamino-5,5-dimethyl-3-thiazoline-2-acetic acid which is condensed with dimethyl phosphite to produce .alpha.-triphenylmethylamino-5,5-dimethyl-4(0,0-dimethylphosphono)-thiazol idine-2-acetic acid which is cyclized to 6-triphenylmethylamino-2,2-dimethyl-3-(0,0-dimethylphosphono)penam and the latter is subsequently deblocked and acylated.

REFERENCES:
patent: 3311609 (1967-03-01), Cheney et al.
patent: 3668201 (1972-06-01), Gutowski
Heusler, Heluetica Chimica Acta, 55, 388. (1972).
Barton et al., J. Chem Soc., (Perkin I), 599 (1973). -

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