Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-09-28
1997-10-28
Trinh, Ba K.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549511, C07D30514
Patent
active
056819706
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/FR94/00339 dated Mar. 25, 1994.
The present invention relates to a process for the preparation of .alpha.-phenylisoserine derivatives of general formula: ##STR2## in which: Ar represents an aryl radical and R represents a hydrogen atom or an alkyl radical optionally substituted with a phenyl radical and R.sub.1 represents a phenyl radical optionally substituted with one or more atoms or radicals, which may be identical or different, chosen from halogen atoms and alkyl, hydroxyl, alkoxy, alkanoyl, alkanoyloxy, nitro, amino, alkylamino, dialkylamino, carbamoyl and trifluoromethyl radicals, the alkyl radicals and the alkyl portions of the other radicals containing 1 to 4 carbon atoms, or alternatively R.sub.1 represents a radical R.sub.2 --O-- in which R.sub.2 represents: alkenyl radical containing 3 to 6 carbon atoms, a cycloalkyl radical containing 3 to 6 carbon atoms or a cycloalkenyl radical containing 4 to 6 carbon atoms, these radicals being optionally substituted with one or more substitutents chosen from halogen atoms and hydroxyl radicals, alkyloxy radicals containing 1 to 4 carbon atoms, dialkylamino radicals in which each alkyl portion contains 1 to 4 carbon atoms, piperidino and morpholino radicals, 1-piperazinyl radicals (optionally substituted in the 4-position 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 4 to 6 carbon atoms, alkenyl radicals containing 4 to 6 carbon atoms, phenyl, cyano and carboxyl radicals, and alkyloxycarbonyl radicals in which the alkyl portion contains 1 to 4 carbon atoms, radicals chosen from halogen atoms and alkyl radicals containing 1 to 4 carbon atoms, and alkyloxy radicals containing 1 to 4 carbon atoms, heterocyclic radical optionally substituted with one or more alkyl radicals containing 1 to 4 carbon atoms.
Ar preferably represents a phenyl or .alpha.- or .beta.-naphthyl radical optionally substituted with one or more atoms or radicals chosen from halogen atoms (fluorine, chlorine, bromine and iodine) and alkyl, aryl, aralkyl, alkoxy, alkylthio, aryloxy, arylthio, hydroxyl, hydroxyalkyl, mercapto, formyl, acylamino, aroylamino, alkoxycarbonylamino, amino, alkylamino, dialkylamino, carboxyl, alkoxycarbonyl, carbamoyl, dialkylcarbamoyl, cyano, nitro and trifluoromethyl radicals, it being understood that the alkyl radicals and the alkyl portions of the other radicals contain 1 to 4 carbon atoms and that the aryl radicals are phenyl or .alpha.- or .beta.-naphthyl radicals.
More particularly, Ar represents a phenyl radical optionally substituted with one or more atoms or radicals, which may be identical or different, chosen from halogen atoms and alkyl, alkoxy, amino, alkylamino, dialkylamino, acylamino, alkoxycarbonylamino and trifluoromethyl radicals.
Even more particularly, Ar represents a phenyl radical optionally substituted with a chlorine or fluorine atom or with an alkyl (methyl), alkoxy (methoxy), dialkylamino (dimethylamino) or acylamino (acetylamino) radical.
According to the present invention, the products of general formula (I) are obtained by the action of an anhydride of general formula: product of general formula: ##STR3## in which Ar and R are as defined above and Ph represents a phenyl or .alpha.- or .beta.-naphthyl radical optionally substituted with one or more atoms or radicals chosen from halogen atoms (fluorine, chlorine, bromine and iodine) and alkoxy radicals containing 1 to 4 carbon atoms, alkylthio radicals containing 1 to 4 carbon atoms, dialkylamino radicals in which each alkyl portion contains 1 to 4 carbon atoms, and nitro radicals. More particularly, Ph represents a phenyl radical optionally substituted with one or more radicals, which may be identical or different, chosen from methoxy, methylthio, methylamino, dimethylamino and nitro radicals.
The process is generally carried out by reacting the anhydride of general formula (II) in the presence of hydrogen, optionally under press
REFERENCES:
Palomo et al., Highly Stereoselective Synthesis of .alpha.-Hydroxy .beta.-Amino acids through .beta.-Lactams:Application to the Synthesis of the Taxol and Bestatin Side Chains and Related Systems, Tetrahedron Letters, vol. 31, (44): 6429-6432, (1990).
Furukawa et al. A Steroselective Synthesis of .alpha.-Chloro-.alpha.-phenylacetamide by the Reaction of Optically Active Schiff Base with Dichlorocarbene, Chem. Pharm. Bull., 25, 181-184 (1977).
Denis et al., An Efficient, Enantioselective Synthesis of the Taxol Side Chain, J. Org. Chem., 51:46-50 (1986).
Didier Eric
Leon Patrick
Rhone-Poulenc Rorer S.A.
Trinh Ba K.
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