Process for preparing alpha,omega-diamino acids

Details Process for preparing alpha,omega-diamino acids Process for preparing alpha,omega-diamino acids

1986-10-16

1987-11-10

Shippen, Michael L.

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

Organic compounds

Carboxylic acids and salts thereof

548473, 548477, 548478, 560163, 562561, C07C10124

Patent

active

047058927

ABSTRACT:
An improved process for preparing .alpha.,.omega.-diamino acids, such as D,L-homolysine, 2,8-diaminooctanoic acid, ornithine, lysine, or the like, comprising reaction of phthalic anhydride and an amino alcohol in a hydrocarbon solvent; treatment of the resulting phthalimide--N--(CH.sub.2).sub.n --OH derivative, without isolation thereof, with phosphorus tribromide or phosphorous pentachloride; alkylation of diethyl acetamidomalonate with the phthalimide--N--(CH.sub.2).sub.n --chloride or --bromide of the previous step, in the presence of, particularly, sodium hydride/dimethylformamide; standard acid hydrolysis and decarboxylation; selective protection via copper(II) chelation, N-specific acylation with benzyl chloroformate, and decomposition of the amino acid-copper(II) complex with alkaline thioacetamide; standard t-butoxycarbonyl acylation; and deprotection to obtain the desired .alpha.,.omega.-diamino acids.

REFERENCES:
patent: 3637838 (1972-01-01), Tetenbaum
patent: 4003862 (1977-01-01), Albright
patent: 4515964 (1985-05-01), Boyer
Gaudry, Can. J. Chem., 31, pp. 1060-1063 (1953).
Richards, Can. J. Chem., 60, pp. 2810-2820 (1982).
Ault, "Techniques and Experiments for Organic Chemistry", 4th Ed., pp. 148-149 (1983).

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