Process for the preparation of N-acyl derivatives of 5-aminolevu

Details Process for the preparation of N-acyl derivatives of 5-aminolevu Process for the preparation of N-acyl derivatives of 5-aminolevu

1993-08-24

1994-09-06

Shippen, Michael L.

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

Organic compounds

Carboxylic acids and salts thereof

20415762, 20415769, 549487, 549496, 562450, C07C22900

Patent

active

053449746

ABSTRACT:
The invention relates to a process for the preparation of N-acyl derivatives of 5-aminolevulinic acid of general formula R-CO-NH-CH.sub.2 -CO-CH.sub.2 -CH.sub.2 -COOH, in which R stands for methyl, ethyl, propyl, isopropyl, butyl, phenyl, benzyl, furyl or furfuryl, as well as the hydrochloride of the free acid by acid hydrolysis, characterized in that the 5-hydroxymethyl furfural is condensed with a nitrile in acid solution and the N-acyl-aminomethyl furfural compound obtained is converted by photooxidation into a N-acyl-5-aminomethyl-5-hydroxydihydro-2,5-furan-2-one and the latter is reduced with zinc in acetic acid under ultrasonic treatment to N-acyl-5-aminolevulinic acid and by acid hydrolysis the 5-aminolevulinic hydrochloride is obtained.

REFERENCES:
patent: 3846490 (1974-11-01), Aronova
patent: 4325877 (1982-04-01), Metcalf
patent: 5095114 (1992-03-01), Radunz
patent: 5284973 (1994-02-01), Ebata

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