Tanabe Seiyaku Company, Limited

Hiroshi Horikawa

Kazuhiko Kondo

Tameo Iwasaki

Totaro Yamaguchi

Tadahiro Matsushita

Disclosed is a process for preparing a .beta.-lactam compound represented by the formula: ##STR1## wherein R.sup.1 represents a hydroxy-substituted lower alkyl group or an amino group each of which may be protected; R.sup.2 represents hydrogen atom or an ester residue; X represents a methylene group which may be substituted by a lower alkyl group, sulfur atom or a group represented by the formula: --A--CH.sub.2 -- where A represents sulfur atom, oxygen atom or methylene group; and W represents an active ester residue of hydroxyl group, or a salt thereof, which comprises the steps of treating a 1-aza-3-thia-bicycloalkane compound represented by the formula: ##STR2## wherein R.sup.1, R.sup.2 and X have the same meanings as defined above, or a salt thereof with a base in the presence of a desulfurizing agent and then reacting the resulting compound with an active esterifying agent of hydroxyl group.

Process for preparing .beta.-lactam derivative and synthetic intermediate

A method for removing substituted or unsubstituted allyl group from .beta.-lactam compound having substituted or unsubstituted allyl group-protecting carboxyl group, which comprises treating said .beta.-lactam compound with palladium catalyst in the presence of allyl-scavenger in aqueous organic solvent, by which the substituted or unsubstituted group can be easily and effectively removed under moderate conditions so that the desired compound can be obtained in high yield at low cost.

Method for removing the protecting group for carboxyl group

Process for preparing .beta.-lactam derivative and synthetic

Process for preparing carbapenem derivative of the formula [I], which comprises subjecting azetidinone compound of the formula [II] to intramolecular cyclization reaction together with elimination reaction of the group of --SR.sup.4, followed by re-adding said group of --SR.sup.4 to the 2-position of the carbapenem skeleton of the intramolecularly cyclized compound, which is industrially useful as process for preparing carbapenem antimicrobials or synthetic intermediate therefor. ##STR1## wherein R.sup.1 is protected or unprotected hydroxy-substituted lower alkyl group, R.sup.2 is hydrogen atom or ester residue, R.sup.3 is hydrogen atom or lower alkyl group, and the group of --SR.sup.4 is group which can be used as substituent at 2-position of the carbapenem antimicrobials.

Process for preparing carbapenem derivatives

A method for removing tri-substituted silyl group from .beta.-lactam compound having a tri-substituted silyl group-protecting hydroxy group, which comprises treating with an acid and a fluoride selected from alkali metal fluoride, alkaline earth metal fluoride and hydrogenfluoride of organic or inorganic amine, by which the tri-substituted silyl group can be easily and effectively removed under moderate conditions so that the desired compound can be obtained in high yield at low cost.

Method for removing the protecting group for hydroxy group

A mercaptan compound of the formula ##STR1## wherein R.sup.3 is a hydrogen atom or a lower alkyl group, or a salt thereof.

Mercaptan compound

1-Methylcarbapenem derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen atom or a hydroxy-protecting group, R.sup.2 is hydrogen atom or an ester residue, R.sup.3 is hydrogen atom or a lower alkyl group, or salts thereof, which have excellent antimicrobial activities and are useful as an antimicrobial drug.

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Kawanishi, Japan

Hiroshi Horikawa