Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1977-03-07
1978-11-28
Daus, Donald G.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
2603067C, 260307F, C07D20508, C07D49804
Patent
active
041275683
ABSTRACT:
1-[.alpha.-(Carboxy)-4-hydroxybenzyl]-3.beta.-aminoazetidin-2-one esters are prepared by converting 2-acyl-3,3-dialkyl-7-oxo-.alpha.-[4-(benzyloxy)phenyl]-4-thia-2,6-diazabic yclo[3.2.0]-heptane-6-acetic acid esters with mercuric acetate in an aqueous organic solvent mixture, e.g., in aqueous methanol, to 7-oxo-3-phenyl-.alpha.-[4-(benzyloxy)phenyl]-4-oxa-2,6-diazabicyclo[3.2.0] hept-2-ene-1-acetic acid esters and the latter are reacted with PCl.sub.5 and pyridine to provide the monocyclic 1-[.alpha.-(carboxy)-4-benzyloxybenzyl]-3.beta.-(.alpha.-chlorobenzylidene amino)-4-chloroazetidin-2-one esters. Reduction of the dichloro azetidin-2-one with an organo tin hydride and azobisisobutyronitrile affords the deschloro, 1-[.alpha.-(carboxy)-4-benzyloxybenzyl]-3.beta.-benzylideneaminoazetidin-2 -one ester. The latter is hydrolyzed and the 4-benzyloxy group is cleaved via catalytic hydrogenolysis to yield an ester of 1-[.alpha.-(carboxy)-4-hydroxybenzyl]-3.beta.-aminoazetidin-2-one. The 3.beta.-amino ester is useful for the preparation of the antibiotic FR 1923 (nocardicin).
REFERENCES:
patent: 4075219 (1978-02-01), McShane
Sheehan et al. in "Molecular Modification of Drug Design" (ACS, 1964), p. 23.
Cooper Robin D. G.
Koppel Gary A.
McShane Lawrence J.
Berch Mark L.
Daus Donald G.
Eli Lilly and Company
Scanlon William B.
Whale Arthur R.
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