Substantially pure enantieners of 2-azabicyclo(2.2.1)hept-5-en-3

Details Substantially pure enantieners of 2-azabicyclo(2.2.1)hept-5-en-3 Substantially pure enantieners of 2-azabicyclo(2.2.1)hept-5-en-3

1994-11-08

1996-03-12

Naff, David M.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

435121, 435128, 435136, 435147, 435227, 435280, 514408, 514418, 514419, 514676, 514740, 548543, A01N 4338, C07C 700, C12N 978, C07D20712

Patent

active

054986257

ABSTRACT:
Lactams of 1-amino-3-carboxylic acid cyclic compounds are produced in enantiomeric form, together with an enantiomer of the corresponding ring-opened amino-acid or ester, by reaction of the racemic lactam with a novel lactamase. The products are useful in the synthesis of chiral carbocyclic nucleotides. The enantiomer is preferrably 2-azabicyclo(2.2.1)hept-5-en-3-one. It is desirable to isolate the enantiomer comprising predominantly the (+) enantiomer and a residual amount of the (-) enantiomer, wherein the (+) enantiomer is present in an enantiomeric excess of at least about 88% over the (-) enantiomer or the enantiomer comprising predominantly the (-) enantiomer and a residual amount of the (+) enantiomer, wherein the (-) enantiomer is present in an enantiomeric excess of at least about 98% over the (+) enantiomer.

REFERENCES:
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Chemical Abstracts, vol. 93, No. 3, Jul. 21, 1980, p. 738, abstract No. 26739t, Columbus, OH; R. D. Allan et al.: "Synthesis of analogs of GABA. III. All four stereoisomers of 3-aminocyclopentanecaroxylic acid and a stereochemical correlation with amidinomycin", Aust. J. Chem., 1979, 31(11), 2517-21.
R. D. Allan et al.: "N-Synthesis of Analogues of GABA. XV, Preparation and Resolution of Some Potent Cyclopentene and Cyclopentane Derivatives", Australian Journal of Chemistry, 1986, 39(6), 855-864.
Chemical Abstracts, vol. 91, No. 25, Dec. 17, 1979, p. 25, abstract no. 204205j, Columbus, OH; G. A. R. Johnston et al.: "Stereospecific actions of GABA analogs", and ADV Pharmacol Ther., Proc. Int. Congr. Pharmacol, 7th 1978 (Pub. 1979) 2, 11-18.
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