Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1997-04-25
1999-03-02
Burn, Brian M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560122, 562457, 562504, C07C26100, C07C 6974, C07C22900, C07C 6106
Patent
active
058773436
ABSTRACT:
The process according to the invention for the preparation of enantiomerically pure cyclopentane-.beta.-amino acids of the general formula (I) ##STR1## in which A and D have the meanings given in the description, is characterized in that meso-dicarboxylic acid anhydrides are first converted by asymmetric alcoholysis with allyl alcohols and in the presence of a chiral amine base present in enantiomerically pure form, in inert solvents, via the intermediate enantiomerically pure salt stage, into the enantiomerically pure dicarboxylic acid monoesters, in a further step these dicarboxylic acid monoesters are intermediately converted, in the sense of a Curtius rearrangement by reaction with azides, into the corresponding acid azides, and are subsequently converted into the corresponding rearranged isocyanates and the isocyanates are then reacted with allyl alcohols to give the compounds of the general formula (VII), and finally the cyclopentane-.beta.-amino acids of the general formula (I) are obtained by splitting off the urethane and ester function.
REFERENCES:
patent: 3560565 (1971-02-01), Childress et al.
patent: 5037809 (1991-08-01), Miyauchi et al.
Diphenylphosphonyl Azide. A New, Convienient Reagent for a Modified Curtius Reaction and for the Peptide Synthesis. J. An. Chem. Soc., 94:17, pp. 6203-6205, 1972 Yamada et al.
Database WPIDS on STN, DNC No. C90-108501, `Cis-2-amino cyclopentane-carboxylic acid derivs.--used as antimicrobials for agricultural and horticultural use.` Abstract of JP 02174753, 1990.
J.Antibiot. (1991), 44(5), 546-549.
Chenevert et al., Tetrahedron: Asymmetry (1992), 3(2), 199-200.
Furuta et al., Tetrahedron Letters, (1987), 28(4) 5841-44.
Bayer Aktiengesellschaft
Burn Brian M.
Davis Brian J.
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