Method of producing 2-azetidinone-1-sulfonic acid compounds

Details Method of producing 2-azetidinone-1-sulfonic acid compounds Method of producing 2-azetidinone-1-sulfonic acid compounds

1982-12-30

1985-08-06

Berch, Mark L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602454, 2603303, 2603309, 26050112, 544238, 544279, 544316, 544319, 544335, 544336, 544359, 544408, 546114, 546122, 546153, 546157, 546172, 546208, 546275, C07D20508, C07D40312, C07D40306, C07D40112

Patent

active

045334951

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates in one aspect to a method of producing 2-azetidinone-1-sulfonic acid compounds which are useful intermediates for the production of antimicrobial agents having improved antimicrobial and .beta.-lactamase-inhibitory activities and in another aspect to materials for use in said method.


BACKGROUND TECHNOLOGY

Recently, a new type of .beta.-lactam antibiotic having a sulfo group in 1-position has been found to be recoverable from nature sources and reported [Nature 289, 590 (1981), 291, 489 (1981)]. Syntheses of compounds analogous thereto have also been reported (e.g. Japanese Published unexamined patent application Nos. 164672/1970 and No. 125362/1971). In the latter report is a description of a method for synthesis of 2-azetidinone-1-sulfonic acid compound having a substituent group in 4-position. This method involves a long and complicated series of reaction steps and there has not been developed an expedient synthetic process.


DISCLOSURE OF THE INVENTION

This invention relates to a method of producing an 2-azetidinone-1-sulfonic acid compound of the formula: ##STR2## [R is an organic residue derived by removal of one hydrogen atom attached to a carbon atom of an organic compound; R.sup.1 is an acylated or protected amino group or an azide group; Z.sup..sym. is a lipophilic quaternary ammonium group] and a novel compound used in the above-mentioned method and having the formula:
The studies conducted by the present inventors led to the finding that if a compound (II) is reacted with a reactive derivative of a carboxylic acid of the formula: the desired compound (I) can be produced in good yield and at low cost and that, while some species of the compound (I) thus obtained have excellent antimicrobial activity of their own, the compound (I) generally is a useful intermediate that can be easily transformed into a compound of the formula: ##STR3## [R.sup.1' is an acylated amino group; R' is an organic residue derived by removal of one hydrogen atom attached to a carbon atom of an organic compound, which may be the same as or different from R] which has excellent antimicrobial and .beta.-lactamase inhibitory activities. This invention has been accomplished on the basis of the above finding.
This invention is, therefore, directed to:
(1) a method of producing an 2-azetidinone-1-sulfonic acid compound (I) characterized by reacting a compound (II) with a reactive derivative of a carboxylic acid (II) in the presence of a base; and
(2) a compound (II).
In the foregoing formulas (I), (II) and (III), the symbol R and R' each is an organic residue attached to the 2-azetidinone nucleus at the 4-position through a carbon atom in said organic residue, or to the group: --CH.dbd.N--SO.sub.3.sup..crclbar. Z.sup..sym.. Such organic residue includes, for example, alkyl, cycloalkyl, alkenyl, alkynyl, cycloalkenyl, aryl, a heterocyclic group, and the like, which may optionally be substituted by one or more substituents. Hereinafter, in this specification, any group which may optionally be substituted will be designated by a superscript asterisk "*". For example, an alkyl which may optionally be substituted will be represented by "alkyl*". In such cases, the number of the substituents is not restricted to one, and some substituted groups may have two to a few substituents which may be the same or different. The alkyl is preferably a straight or branched-chain lower alkyl having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl or the like. The cycloalkyl preferably has 3 to 8 carbon atoms and includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, etc. The alkenyl is preferably a straight or branched-chain lower alkenyl having 2 to 6 carbon atoms such as vinyl, allyl, isopropenyl, 2-methallyl, 2-butenyl, 3-butenyl or the like. The alkynyl is preferably a straight or branched-chain lower alkynyl having 2 to 6 carbon atoms such as ethynyl, 1-propynyl,

REFERENCES:
patent: 4159279 (1979-06-01), Smith et al.
Imada et al., Nature, 289, 590, (1981).
Sykes et al., Nature, 291, 489, (1981).
European Patent Publication No. 0021678.

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