High percentage beta-yield synthesis of carbapenem intermediates

Details High percentage beta-yield synthesis of carbapenem intermediates High percentage beta-yield synthesis of carbapenem intermediates

1986-02-24

1988-09-20

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 14, 546341, 548110, 548214, 548342, 549 4, 549 79, 549214, 549499, 556423, C07D20508, C07D40112, C07D40312, C07F 718

Patent

active

047726830

ABSTRACT:
Disclosed herein is a novel process using novel silyl enol ether intermediates of the formula ##STR1## to generate novel azetidione thiolester intermediates of the formula ##STR2## which can be used to form 1-.beta.-alkyl carbapenem antibiotics. It has now been discovered that if the R.sup.4 group is selected from a small group of moieties having the formula: ##STR3## an increased .beta.-yield of up to approximately 100% can be obtained.

REFERENCES:
patent: 4683296 (1987-07-01), Ueda et al.
Shih, David H., et al., Heterocycles, (vol. 21, No. 1, 1984), pp. 29-40.
Merck, Drugs of the Future, (Vol. 9, No. 5, 1984) pp. 3360338 at 337.
Kim, Tet. Letters, 28, 507-510, (1987).
Tajima, Tet. Letters, 26(5), 673-676, (1985).
Gennari et al., Tet. Letters, 26 (6), 797-800, (1985).

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