Azetidinone intermediates for 1-carba(dethia)caphalosporins

Details Azetidinone intermediates for 1-carba(dethia)caphalosporins Azetidinone intermediates for 1-carba(dethia)caphalosporins

1988-06-06

1989-12-05

Berch, Mark L.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

C07D70508, C07D40306, C07D40912, C07F 710

Patent

active

048853623

ABSTRACT:
Azetidinone-2 intermediates represented by the formula ##STR1## wherein R is phenyl, phenoxy or thienyl, R.sub.1 is --CH.dbd.CH--COOR.sub.1 ' wherein R.sub.1 ' is an ester, e.g., benzyl; --CH.sub.2 CH.sub.2 COR.sub.2 wherein R.sub.2 is OH or imidazol-1-yl; --CH.sub.2 CH.sub.2 C(O)CH.sub.2 COOR.sub.1 ' where R.sub.1 ' is an ester, e.g., p-nitrobenzyl; and R', R" and R'" are C.sub.1 -C.sub.4 alkyl, aryl or aralkyl; are converted to 1-carba(dethia)cephalosporin antibiotics. Preferably, R is phenoxy and the 1-silyl group is dimethyl-t-butylsilyl. Also provided is 3.beta.-phenoxyacetylamino-4.beta.-(2-carboxyethyl)azetidinone, likewise useful in the preparation of 1-carbacephalosporin antibiotics.

REFERENCES:
patent: 4226866 (1980-10-01), Christensen et al.
patent: 4407815 (1983-10-01), Pearson
patent: 4665171 (1987-05-01), Evans et al.
Hatanaka et al., "A Simple Synthesis of (.+-.)-1-Carbacephem Derivatives", Tetrahedron Letters, vol. 24 (No. 44), pp. 4837-4838, 1983.

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