Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen bonded directly to ring carbon of the purine ring...
Patent
1993-11-12
1996-06-11
Berch, Mark L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen bonded directly to ring carbon of the purine ring...
562124, C07B 5700, C07D47318, A61K 3152
Patent
active
055257267
ABSTRACT:
Racemic Feist's acid is treated with (R)-(+) -.alpha.-methylbenzylamine to yield (1R-trans)-3-methylene -cyclopropane-1,2-dicarboxylic acid, (R)-.alpha.-methylbenzyl-amine (1:1) salt. This salt can then be converted to (1R-trans)-3-methylene-1,2-cyclopropanedicarboxylic acid, dimethyl ester which is an intermediate in the preparation of the antiviral agent [1R-(1.alpha.,2.beta.,3.alpha.)]-2-amino-9-[2,3-bis(hydroxymethyl)cyclobut yl]-1,9-dihydro-6H-purin-6-one. The improved process also enables the recovery of racemic Feist's acid from the resolution.
REFERENCES:
patent: 4499079 (1985-02-01), Gordon et al.
patent: 5064961 (1991-11-01), Bisacchi et al.
patent: 5126345 (1992-06-01), Slusarchyk et al.
patent: 5153352 (1992-10-01), Norbeck et al.
patent: 5235052 (1983-08-01), Pariza
Ichikawa, JCS Chem Comm 1989, 1919-1921.
Yamamoto, J. Antibiotics 1989, 1854-1859.
Braitman, Antimicro Agents and Chemotherapy 35, pp. 1464-1468 (1991).
Norbeck, J Med Chem 33, 1281-1285 (1990).
Clement, Transplantation Proc. 23, (3), Supp 3, pp. 159-161 (1991).
Doering et al., "Stereochemistry Of The Methylenecyclopropane Rearrangement", Tetrahedron, vol. 26, pp. 2825-2835 (1970).
Ettlinger et al., "The Cis-Isomer of Feist's Acid", Chemistry and Industry, 1957, p. 891.
Bottini et al., "The Nuclear Magnetic Resonance . . . ", J. Org. Chem., 1956, vol. 21, pp. 1169-1170.
Gajewski, "Hydrocarbon Thermal Degenerate . . . ", Jour. Amer. Chem. Soc., vol. 93, pp. 4450-4458 (1971).
SUCR-P, Chem. Abst., 84, 105082(r) (1975).
DeVos et al., J. Amer. Chem. Soc., 104, 4282 (1982).
Aldrich Catalog, 1992, pp. 774-775.
Godfrey Jr. Jollie D.
Kissick Thomas P.
Mueller Richard H.
Singh Janak
Berch Mark L.
Davis Stephen B.
E. R. Squibb & Sons Inc.
LandOfFree
Process for the preparation of an antiviral agent 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 preparation of an antiviral agent, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of an antiviral agent will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-352781