Process for 3-iodomethyl cephalosporins

Details Process for 3-iodomethyl cephalosporins Process for 3-iodomethyl cephalosporins

1980-02-20

1981-05-05

Rizzo, Nicholas S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544 21, 544 17, 544 22, C07D50104

Patent

active

042660491

ABSTRACT:
A process for preparing 3-iodomethyl cephalosporins wherein a 3-alkanoyloxymethyl or 3-carbamoyloxymethyl cephalosporin is reacted with a trialkylsilyl iodide, e.g. trimethylsilyl iodide. Certain cephalosporin esters, e.g., benzhydryl esters, undergo cleavage and cephalosporin sulfoxides are reduced to the sulfide form in the process. The 3-iodomethyl cephalosporins are useful intermediates for antibiotics.

REFERENCES:
patent: 3658799 (1972-04-01), Eardley et al.
patent: 4042585 (1977-08-01), Koppel
Karapy et al., Tetrahedron Letters No. 30, pp. 2625-2628.
Jung et al., JACL 99 (3), 968 (1977).
Ho et al., Proc. Natl. Acad. Sci. v & A 75, pp. 4-6, (1970).
Ho et al., Synthesis, 417 (1977).
Morita et al., J. Chem. Soc. Chem. Comm. p. 874 (1970).
Olah et al., Synthesis 583 (1977).
Olah et al., Synthesis 61 (1979).
Mangia et al., Tetrahedron Letters No. 52, pp. 5219-5220 (1978).
Lott et al., J. Chem. Soc. Chem. Comm. 495 (1979).

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