Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-08-11
1996-07-30
Berch, Mark
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
540302, 540310, C07D20508, C07D22700, C07D48704, C07D49904
Patent
active
055413170
ABSTRACT:
Compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen or a hydroxy-protecting group; R.sup.2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R.sup.3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR.sup.5 R.sup.6, where Y is oxygen or sulfur, and R.sup.5 and R.sup.6 are each alkyl, aryl or aralkyl, or R.sup.5 and R.sup.6 and the nitrogen to which they are attached together form a heterocyclic group; is R.sup.4 hydrogen or an amino-protecting group; and Z is sulfur or oxygen; are valuable intermediates in the preparation of carbapenem compounds and retain a desirable configuration during conversion to such carbapenem compounds. Penem and carbapenem compounds having a group of formula --SA' are prepared from a corresponding compound having a substituted thio, sulfinyl or sulfonyl group at this position by reaction with a compound A'SH (where A' is an organic group) in the presence of a salt of a metal of Group II or III of the Periodic Table.
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Sowin, et al, "Enantioselective Synthesis of the 1.beta.-Methylcarbapanems via Cycloaddition of 3-Siloxypentadiene and 4-Acetoxyazetidinone", J.A.C.S., 53, 4154 (1988).
Guthikonda et al, "Structure-Activity Relationships in the 2-Arylcarbapenem Series: Synthesis of 1-Methyl-2-arylcarbapenems", J. Med. Chem., 30, 871 (1987).
Kim et al, "Stereoselective Synthesis of 1-.beta.-Methylcarbapenem", Tetrahedron Letters, 28, 507-510 (1987).
Hirai Koichi
Iwano Yuji
Koyama Hiroo
Nishi Takahide
Oda Kozo
Berch Mark
Sankyo Company Limited
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