Process for preparing azetidin-2-one derivatives

Details Process for preparing azetidin-2-one derivatives Process for preparing azetidin-2-one derivatives

1992-07-07

1994-06-21

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540362, 556413, 558275, 558276, 560 29, 564 93, C07D20508, C07B 4306

Patent

active

053229398

ABSTRACT:
A process for preparing an azetidin-2-one derivative represented by formula (2): ##STR1## wherein R.sup.4 and R.sup.5, which may be the same or different, each represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, or an alkyl group having from 1 to 8 carbon atoms substituted with an alkoxy group, an acyl group, or an alkoxycarbonyl group; R.sup.6 represents a protective group for an amino group; and R.sup.7 represents a vinylidene group of formula ##STR2## or an acetylene group of formula ##STR3## wherein R.sup.2 and R.sup.3, which may be the same or different, each represents a hydrogen atom or an alkyl group having from 1 to 8 carbon atoms; and R.sup.8 represents an alkyl group having from 1 to 8 carbon atoms corresponding to R.sup.2 or R.sup.3, which comprises reacting a propargyl alcohol derivative represented by formula (1): ##STR4## wherein R.sup.1 represents an alkyl group having from 1 to 6 carbon atoms, a phenyl group, or a halogen-substituted phenyl group; R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are as defined above, with carbon monoxide in the presence of a palladium complex. The compound (2), an intermediate of penem antibiotics, can be obtained through one reaction step in good yield.

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