Unsymmetrical azetidinone aldehyde disulfides and process

Details Unsymmetrical azetidinone aldehyde disulfides and process Unsymmetrical azetidinone aldehyde disulfides and process

1980-04-07

1981-11-24

Berch, Mark L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602454, 2603303, 2603473, 544 90, C07D20508, C07D49804, C07D40312, C07D40512

Patent

active

043023916

ABSTRACT:
Aryl 4R[1-(2-N-3-methyl-4-al-Z-but-2-ene-oate)-2-oxo-3S-acylamino azetidinone]disulfides are prepared by reacting the corresponding 7.alpha.-acylamino-2.alpha.-alkoxy-3-methyl-3-cephem-4-carboxylates first with either phenylsulfenyl chloride or a monosubstituted-phenylsulfenyl chloride where the substituent is either chloro, methoxy, methyl or acetoxy. The disulfide compounds produced in this invention are intermediates in the synthesis of the 7.beta.-acylamino-7.alpha.-alkoxy-3-methyl 1-oxa .beta.-lactam acids, a class of antibiotic compounds.

REFERENCES:
patent: 3872086 (1975-08-01), Barton et al.
patent: 3954732 (1976-05-01), Kamiya et al.
patent: 4066641 (1978-01-01), Hamashima
patent: 4071513 (1978-01-01), Kim
Barton et al., Chem. Comm., 1137 (1971).
Kamiya et al., Tet. Letters, 13001 (1973).
Kim et al., Tet. Letters, 409 (1978).
Yoshida et al., Chem. Pharm. Bull. 24, 362 (1976); 25, 2082 (1977).
Glaxo, Chem. Abs. 91, 157730q, (1979).
Woodward et al., Chem. Abs. 90, 54804s.

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