Process for the preparation of an antiviral agent

Details Process for the preparation of an antiviral agent Process for the preparation of an antiviral agent

1991-10-02

1993-02-09

Shippen, Michael L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

544276, 560124, 562401, C07C 6104

Patent

active

051854635

ABSTRACT:
Racemic Feist's acid is treated with (R)-(+)-.alpha.-methylbenzylamine to yield (1R-trans)-3-methylenecyclopropane-1,2-dicarboxylic acid, (R)-.alpha.-methylbenzylamine (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)cyclobutyl]-1,9-dihydro-6H-pur in-6-one. The improved process also enables the recovery of racemic Feist's acid from the resolution.

REFERENCES:
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).
Ahmad, copending commonly assigned application Ser. No. 692,752 filed Apr. 29, 1991,

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