Process for the production of 4-substituted azetidinone derivati

Details Process for the production of 4-substituted azetidinone derivati Process for the production of 4-substituted azetidinone derivati

1996-11-04

1998-08-11

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20508, C07D40306, C07D41306, C07D41706

Patent

active

057928614

ABSTRACT:
The present invention provides a process for the production of a 4-substituted azetidinone. The process comprises reacting ##STR1## wherein R represents a hydrogen atom or a protecting group for N, R.sup.1 represents an alkyl which may be a substituent having an unprotected or protected hydroxyl group; and Z represents a leaving group; with ##STR2## wherein R.sup.2 represents hydrogen or alkyl, R.sup.3 and R.sup.4 each represent hydrogen, alkyl, alkenyl, alkynyl, phenyl, cycloalkyl, or naphthyl, or R.sup.3 and R.sup.4, together with the carbon atom to which they are bonded, form a ring system; X and Y each represent oxygen, sulfur or N-r.sup.1, wherein r.sup.1 represents a hydrogen atom or lower alkyl; A, B, D and E each represent nitrogen or C-r.sup.2, wherein r.sup.2 represents hydrogen, halogen, lower alkyl or lower alkoxy, provided that at least two of A, B, D and E are C-r.sup.2 ; and a ring involving G, J and K has two carbon/carbon double bonds therein and one of G, J and K represents oxygen, sulfur or N-r.sup.1 while the remaining two represent C-r.sup.2 ; in the presence of

REFERENCES:
patent: 5442055 (1995-08-01), Iwasaki
patent: 5731431 (1998-03-01), Nakagawa
Tetrahedron letters, vol. 27, No. 47, pp. 5687-5690, "Simple and Highly Diastereoselective ... Enolates", Deziel et al. 1986.
Tetrahedron letters, vol. 28, No. 52, pp. 6625-6628, "A Highly Stereoselective Synthesis of a Key ... Derivatives", Ito et al. 1987.
Tetrahedron Letters, vol. 30, No. 41, pp. 5631-5634, "A Novel Synthesis of the 1.beta.-Methycarbapenem ... Derivative", Ito et al. (1989).
Patent Abstracts of Japan, vol. 12, No. 132, "4-Substituted ... Compound", Sugimura MASAO, Apr. 11, 1987, Jap. Pat. No. 62252786.

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