Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1990-08-03
1992-12-29
Springer, David B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548453, C07D20952, C07D20912
Patent
active
051753065
ABSTRACT:
The invention relates to a process for resolving racemic mixtures of bicyclic imino-.alpha.-carboxylic esters into the components by crystallization of diastereomeric salts, which comprises preparing the salts of the racemic esters with optionally active N-acylated R- or S-aminocarboxylic acids which contain a phenyl nucleus, recrystallizing them from an organic solvent, decomposing the precipitated, optically homogeneous diastereomeric salts in a manner known per se, and isolating the enantiomers and, where appropriate, converting the latter into the free acids by hydrolysis in a manner known per se. The invention also relates to optically pure compounds of the formula ##STR1## and to diastereomeric salts of these compounds, in which two of the radicals A, B.sup.1, B.sup.2 and C form a carbon chain and the other denote hydrogen, and R is an esterifying group.
REFERENCES:
patent: 4374847 (1983-02-01), Gruenfeld
patent: 4508729 (1985-04-01), Vincent et al.
patent: 4525301 (1985-06-01), Henning et al.
patent: 4558064 (1985-12-01), Teetz et al.
patent: 4558065 (1985-12-01), Urbach et al.
patent: 4562202 (1985-12-01), Urbach et al.
patent: 4587258 (1986-05-01), Gold et al.
patent: 4591598 (1986-05-01), Urbach et al.
patent: 4614805 (1986-09-01), Urbach et al.
patent: 4620012 (1986-10-01), Henning et al.
patent: 4659838 (1987-04-01), Lerch
patent: 4668797 (1987-05-01), Urbach et al.
patent: 4684662 (1987-08-01), Henning et al.
patent: 4691022 (1987-09-01), Henning et al.
patent: 4714708 (1987-12-01), Urbach et al.
patent: 4727160 (1988-02-01), Teetz et al.
patent: 4808573 (1989-02-01), Gold et al.
patent: 4818749 (1989-04-01), Gold et al.
patent: 4831157 (1989-05-01), Gold et al.
Leonard et al., J. Am. Chem. Soc., 77, 439 (1955).
Leonard et al., J. Am. Chem. Soc., 78, 3457 (1956).
Leonard et al., J. Am. Chem. Soc., 78, 3463 (1956).
Leonard et al., J. Am. Chem. Soc., 81, 5627 (1959).
Koelsch et al., J. Org. Chem., 26, 1104 (1961).
Griot et al., Helv. Chim. Acta, 42, 121 (1959).
Bonnett et al., J. Chem. Soc., 2087 (1959).
Battersby et al., J. Chem. Soc., 4333 (1958).
Rosenblatt et al., The Chemical of Functional Groups. Supplement F: The Chemistry of Amino, Nitroso and Nitro Compounds And Their Derivatives, Part II, S. Patai, ed., Wiley & Sons: New York, 1982, pp. 1100-1104.
L. W. Haynes, Enamines, A. G. Cook, ed., Marcel Decker, Inc.: 1969, pp. 68-79, 261-269, 413.
Fieser & Fieser, Reagents For Organic Synthesis, vol. 1, pp. 644-651 (1967).
Boehme et al., Iminium Salts in Organic Chemistry, Part I (E. C. Taylor, ed.), Wiley & Sons: New York, 1976, p. 143.
S. Dayagi et al., The Chemistry Of Functional Groups. The Chemistry Of The Carbon-Nitrogen Double Bond, S. Patai, ed., Wiley & Sons: New York, 1970, p. 119.
W. Greenlee et al., J. Med. Chem., 28, 434-442 (1985).
K. Ogawa et al., J. Chem. Soc., Perkin Trans. I, 3031-3035 (1982).
R. Bacon and D. Stewart, J. Chem. Soc. (C), 1384-1387 (1966).
R. Bacon et al., J. Chem. Soc. (C), 1388-1389 (1966).
Patchett et al., Nature, 288, 280-283 (1980).
Booth et al., Chemistry and Industry, 466-467 (1956).
Booth et al., J. Chem. Soc., Part I, 1050-1054 (1959).
Murakoshi et al., Chemical Abstracts, 61, 9465(e)(1964).
Cushman et al., Fed. Proc., 38 (13), 2778-2782 (1979).
Houben-Weyl, Methoden der Organischen Chemie, 7(2b), 1403-1404 (1976).
Katritskaya, Dzh. Lagorskaya Khimia Geterosikl. Soedin., Moskow 1963, pp. 155-158.
Anderson, Jr. et al., J. Org. Chem. 43(1), 54-57 (1978).
Bertho et al., "Synthesen In Der 2-Azabicyclo[0.3.3]-octan-Reihe", Chemische Berichte, 92(7), 2218-2235 (1959).
Farkas et al., J. Org. Chem., 22, 1261-1263 (1957).
Taylor et al., J. Org. Chem., 38(16), 2817-2821 (1973).
Taylor et al., Heterocycles, 25, 343-345 (1987).
English language translation of Mitzlaff et al., Liebig's Ann. Chem., 1713-1733 (1978).
Chem. Berichte 86: 1524-1528 (1953).
Quarterly Reviews 25: 323-341 (1971).
Chem. Abst. 49/1955/3009c.
Geiger Rolf
Langner Dietrich
Teetz Volker
Hoechst Aktiengesellschaft
Springer David B.
LandOfFree
Process for the resolution of racemates of optically active bicy does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the resolution of racemates of optically active bicy, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the resolution of racemates of optically active bicy will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1888599