Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1995-04-05
1998-03-10
Trinh, Ba K.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
562450, C07C 5106, C07C22908
Patent
active
057263469
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/FR93/00966, dated Oct. 4, 1993.
DESCRIPTION OF THE INVENTION
The present invention relates to a process for the stereoselective preparation of a .beta.-phenylisoserine derivative of general formula: ##STR2## in which Ar represents an aryl radical, substituted with one or more identical or different atoms or radicals chosen from halogen atoms, alkyl radicals containing 1 to 4 carbon atoms and alkoxy radicals containing 1 to 4 carbon atoms, or a radical R.sub.1 --O in which R.sub.1 represents: 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 being optionally substituted with one or more substituents chosen from halogen atoms and hydroxyl radicals, alkyloxy radicals containing 1 to 4 carbon atoms, dialkylamino radicals in which each alkyl portion contains i to 4 carbon atoms, piperidino or morpholino radicals, 1-piperazinyl radicals (optionally substituted at position 4 with an alkyl radical containing 1 to 4 carbon atoms or with a phenylalkyl radical in which the alkyl portion contains 1 to 4 carbon atoms), cycloalkyl radicals containing 3 to 6 carbon atoms, cycloalkenyl radicals containing 4 to 6 carbon atoms, phenyl, cyano or carboxyl radicals or alkyloxycarbonyl radicals in which the alkyl portion contains i to 4 carbon atoms, radicals chosen from halogen atoms and alkyl radicals containing 1 to 4 carbon atoms or alkyloxy radicals containing 1 to 4 carbon atoms, radical optionally substituted with one or more alkyl radicals containing 1 to 4 carbon atoms, on the understanding that the cycloalkyl, cycloalkenyl or bicycloalkyl radicals can be optionally substituted with one or more alkyl radicals containing 1 to 4 carbon atoms, and methoxymethyl, 1-ethoxyethyl, benzyloxymethyl, 2,2,2-trichloroethoxymethyl, tetrahydrofuranyl,-tetrahydropyranyl and .beta.-(trimethylsilyl)ethoxymethyl radicals, trialkylsilyl radicals in which the alkyl radicals contain 1 to 4 carbon atoms, or --CH.sub.2 --Ph in which Ph represents a phenyl radical optionally substituted with one or more identical or different atoms or radicals chosen from halogen atoms, alkyl radicals containing 1 to 4 carbon atoms and alkoxy radicals containing 1 to 4 carbon atoms.
Preferably, Ar represents a phenyl or .alpha.- or .beta.-naphthyl radical optionally substituted with one or more atoms or radicals chosen from halogen (fluorine, chlorine, bromine, iodine) atoms and alkyl, alkenyl, alkynyl, aryl, arylalkyl, alkoxy, alkylthio, aryloxy, arylthio, hydroxyl, hydroxyalkyl, mercapto, formyl, acyl, acylamino, aroylamino, alkoxycarbonylamino, amino, alkylamino, dialkylamino, carboxyl, alkoxycarbonyl, carbamoyl, dialkylcarbamoyl, cyano, nitro and trifluoromethyl radicals, on the understanding that the alkyl radicals and alkyl portions of the other radicals contain 1 to 4 carbon atoms, that the alkenyl and alkynyl radicals contain 3 to 8 carbon atoms and that the aryl radicals are phenyl or .alpha.- or .beta.-naphthyl radicals.
More especially, Ar represents a phenyl radical optionally substituted with one or more identical or different atoms or radicals chosen from halogen atoms and alkyl, alkoxy, amino, alkylamino, dialkylamino, acylamino, alkoxycarbonylamino and trifluoromethyl radicals.
Still more especially, Ar represents a phenyl radical optionally substituted with a chlorine or fluorine atom or with an alkyl (methyl), alkoxy (methoxy), dialkylamino (dimethylamino), acylamino (acetylamino) or alkoxycarbonylamino (tert-butoxycarbonylamino) radical.
Of even more special importance are the products of general formula (I) in which Ar represents a phenyl radical, R represents a phenyl or tert-butoxy radical and G.sub.1 represents a benzyl or p-methoxybenzyl radical.
The products of general formula (I), and especially those for which G.sub.1 represents --CH.sub.2 --Ph, which are new products con
REFERENCES:
patent: 4924011 (1990-05-01), Denis et al.
Mc Omie J. F, "Protective Groups in Organic Chemistry", pp. 98-100, 1973.
Greene et al, "Protective Groups in Organic Synthesis", pp. 10-11, 413, 1991.
Denis Jean-Noel
Greene Andrew-Elliot
Kanazawa Alice
Rhone-Poulenc Rorer S.A.
Trinh Ba K.
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