Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1979-05-21
1981-01-06
Berch, Mark L.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
C07D49804
Patent
active
042435870
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: 3950352 (1976-04-01), Wolfe
patent: 4158004 (1979-06-01), Koppel et al.
patent: 4159984 (1979-07-01), Yoshioka
Stoodley et al., J.C.S., Perkins I, 1974, 181.
Yoshioka et al. Chem. Abs. 88, 50635y, (1977).
Cooper Robin D. G.
Koppel Gary A.
McShane Lawrence J.
Berch Mark L.
Eli Lilly and Company
Scanlon William B.
Whale Arthur R.
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