Bicyclic azetidinone intermediates

Details Bicyclic azetidinone intermediates Bicyclic azetidinone intermediates

1986-04-29

1987-04-07

Berch, Mark L.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540215, 540229, 540230, C07D51304, C07D50130, C07D50142, C07D50152

Patent

active

046562648

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD AND DISCLOSURE OF THE INVENTION

The present invention relates to novel azetidinone compounds.
The azetidinone compounds of the present invention are novel compounds undisclosed in literature. They are represented by the formula ##STR3## wherein R.sup.1 represents a substituted or unsubstituted phenyl group, R.sup.2 represents a carboxyl-protecting group, X represents a hydrogen atom or chlorine atom and Y represents --I, --ONO.sub.2, --OH, ##STR4## or --SR.sup.4 in which R.sup.3 is a lower alkyl group or --OR.sup.5 (wherein R.sup.5 is a halogen-containing lower alkyl group) and R.sup.4 is a substituted or unsubstituted, 5-membered aromatic heterocyclic residue containing sulphur and/or nitrogen atom or atoms.
The azetidinone derivatives of the formula (I) are useful as intermediates for synthesizing cephalosporin-type antibiotics. For example, a cephalosporin compound of the formula (VII) useful as an antibacterial agent can be prepared from the compound of the present invention according to a reaction equation shown below. ##STR5##
In the reaction equation, R.sup.1, R.sup.2 and Y are as defined above.
Examples of the substituted or unsubstituted phenyl groups represented by R.sup.1 in the formula (I) are phenyl, tolyl, xylyl, p-chlorophenyl, p-bromophenyl, p-nitrophenyl, phenyl having protected hydroxyl such as p-methoxyphenyl, etc. Illustrative of carboxyl-protecting groups represented by R.sup.2 are methyl, benzyl, diphenyl methyl, p-nitrophenyl, trichloroethyl, etc. Examples of the lower alkyl groups represented by R.sup.3 are those having 1 to 4 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, etc. Exemplary of the substituted or unsubstituted, 5-membered aromatic heterocyclic residues containing sulphur and/or nitrogen atom or atoms and represented by R.sup.4 are 5-methyl-1,3,4-thiadiazole-2-yl, 1-methyl-1,2,3,4-tetrazole-5-yl, 1-phenyl-1,2,3,4-tetrazole-2-yl, 1,3,4-thiadiazole-2-yl, 1,3-thiazole-2-yl, etc. The halogen-containing lower alkyl groups represented by R.sup.5 include, for example, 2-chloroethyl, 2-bromoethyl, 2,2-dichloroethyl, 2,2'-dibromoethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, etc.
The compound (I) of the present invention can be prepared by using a compound of the formula (IV) ##STR6## wherein R.sup.1 and R.sup.2 are as defined above as the starting material by various processes as stated hereinafter.
The compound (IV) can be prepared by the conventional method, for example, that reported in Tetrahedron Lett. 22, 3193 (1981).
(1) The compound of the present invention represented by the formula ##STR7## wherein R.sup.1 and R.sup.2 are as defined above and Y represents --I or ##STR8## (in which R.sup.3 is as defined above) can be prepared by reacting the starting material (IV) with a nucleophilic reagent of the formula ##STR9## (in which R.sup.3 is as defined above) and M represents sodium or potassium atom in an organic solvent. Useful organic solvents can be any of those capable of dissolving the starting compound (IV) and the nucleophilic reagent, such as acetone, methyl ethyl ketone, methyl-isobutyl ketone or like ketones; methyl formate, ethyl formate, methyl acetate, ethyl acetate or like esters; diethyl ether, tetrahydrofuran, dioxane or like ethers; nitromethane, nitroethane or like nitroalkanes; acetonitrile, propionitrile or like nitriles; methanol, ethanol or like alcohols; dimethylformamide, dimethylacetamides or like amides; dimethylsulfoxide; etc. among which acetone and dimethylsulfoxide are preferred. The amount of the organic solvent is not particularly limited but is usually 1 to 200 times, preferably 2 to 50 times, the weight of the compound (IV). The ratio between the compound (IV) and the nucleophilic reagent can be suitably determined over a wide range. Usually about 1 to about 5 moles, preferably about 1 to about 3 moles, of the latter is used per mole of the former. The reaction is carried out at a temperature of usually about -10 .degree. to about 70.degree. C., preferably about 10.degree. to about 55.degree. C. and is comp

REFERENCES:
Greene, "Protective Groups in Organic Chem" 1981, pp. 152-192.
McOmie, Protective Groups in Organic Chem. 183 (1973).

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