Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1997-07-21
1998-09-22
Daus, Donald G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
548215, 549510, C07D26306
Patent
active
058115501
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION OF THE INVENTION
The present invention relates to a process for the preparation of a 1,3-oxazolidine-5-carboxylic acid of general formula: ##STR3## in which Ar represents an aryl radical, R.sub.1 represents a benzoyl radical or a radical R.sub.2 --O--CO-- in which R.sub.2 represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, phenyl or nitrogenous heterocyclyl radical, and Ph represents an optionally substituted phenyl radical.
More particularly, Ar represents a phenyl or .alpha.- or .beta.-naphthyl radical optionally substituted by one or a number of atoms or radicals, which are identical or different, chosen from halogen atoms (fluorine, chlorine, bromine, iodine) and alkyl, alkenyl, alkynyl, aryl, arylalkyl, alkoxy, alkylthio, aryloxy, arylthio, hydroxyl, hydroxyalkyl, mercapto, formyl, acyl, acylamino, aroylamino, alkoycarbonylamino, amino, alkylamino, dialkylamino, carboxyl, alkoxycarbonyl, carbamoyl, dialkylcarbamoyl, cyano and trifluoromethyl radicals, it being understood that the alkyl radicals and the alkyl portions of the other radicals contain 1 to 4 carbon atoms, the alkenyl and alkynyl radicals contain 3 to 8 carbon atoms and the aryl radicals are phenyl or .alpha.- or .beta.-naphthyl radicals, R.sub.1 represents an optionally substituted benzoyl radical or a radical R.sub.2 --O--CO-- in which R.sub.2 represents a straight or branched alkyl radical containing 1 to 8 carbon atoms, an alkenyl radical containing 2 to 8 carbon atoms, an alkynyl radical containing 3 to 8 carbon atoms, a cycloalkyl radical containing 3 to 6 carbon atoms, a cycloalkenyl radical containing 4 to 6 carbon atoms or a bicycloalkyl radical containing 7 to 11 carbon atoms, these radicals optionally being substituted by one or a number of substituents chosen from halogen atoms and hydroxyl, alkyloxy containing 1 to 4 carbon atoms, dialkylamino, in which each alkyl part contains 1 to 4 carbon atoms, piperidino, morpholino, 1-piperazinyl (optionally substituted in the 4-position by an alkyl radical containing 1 to 4 carbon atoms or by a phenylalkyl radical in which the alkyl part contains 1 to 4 carbon atoms), cycloalkyl containing 3 to 6 carbon atoms, cycloalkenyl containing 4 to 6 carbon atoms, phenyl, cyano, carboxyl or alkyloxycarbonyl, in which the alkyl part contains 1 to 4 carbon atoms, radicals, or a phenyl radical optionally substituted by one or a number of atoms or radicals chosen from alkyl radicals containing 1 to 4 carbon atoms or alkyloxy radicals containing 1 to 4 carbon atoms, or a saturated or unsaturated nitrogenous heterocyclyl radical containing 5 or 6 members and optionally substituted by one or a number of alkyl radicals containing 1 to 4 carbon atoms, it being understood that the cycloalkyl, cycloalkenyl or bicycloalkyl radicals can be optionally substituted by one or a number of alkyl radicals containing 1 to 4 carbon atoms, and Ph represents a phenyl radical substituted by one or a number of electron-donating radicals chosen more particularly from the group of alkoxy radicals containing 1 to 4 carbon atoms.
According to the present invention, an acid of general formula (I) can be obtained by cyclization of a product of general formula: ##STR4## in which Ar, R.sub.1 and Ph are defined as above and X represents a ##STR5## residue of an optically active organic base or a residue --O--R in which R represents an alkyl radical containing 1 to 4 carbon atoms optionally substituted by a phenyl radical, followed by hydrolysis or saponification of the product obtained of general formula: ##STR6## in which Ar, R.sub.1, Ph and X are defined as above.
Generally, the cyclization is performed by carrying out the reaction, preferably in anhydrous medium, in an organic solvent chosen from ethers, esters, ketones, nitrites, optionally halogenated aliphatic hydrocarbons and optionally halogenated aromatic hydrocarbons in the presence of an oxidizing agent such as dichlorodicyanobenzoquinone at a temperature between 0.degree. C. and the boiling temperature of the reaction mixture. Pre
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Denis Jean-Noel
Greene Andrew-Elliot
Kanazawa Alice
Daus Donald G.
Rhone-Poulenc Rorer S.A.
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