SYNTHESIS OF 2-OXAZOLIDINONE DERIVATIVES IN SINGLE REACTOR Russian patent published in 2001 - IPC

FIELD: organic chemistry, chemical technology. SUBSTANCE: invention proposes the improved method of synthesis of (S)-4-{[3-[2-(dimethylamino)-ethyl]-1H-indole-5-yl]-methyl}-2-oxa-zolindinone that involves the following stages: (a) formation of carbamate of the formula (III) from methyl-4-nitro-(L)-phenylalaninate hydrochloride; (b) reduction of compound of the formula (III) to yield methyl-(S)-N-butoxy-carbonyl-4-aminophenylalaninate of the formula (IV) ; (c) reduction of ester methyl group in compound of the formula (IV) to yield (S)-N-butoxycarbonyl-4-aminophenylalanilol of the formula (V) ; (d) ring closure in compound of the formula (V) to yield (S)-4-aminobenzyl-2-oxazolidinone hydrochloride of the formula (VII) ; (e) formation of diazonium salt from compound of the formula (VI) and the following reduction and yielding (S)-4-(4-hydrazinobenzyl)-2-oxazolidinone hydrochloride hydrazine of the formula (VII); f) Fischer's reaction of compound of the formula (VII) to yield (S)-4-{[3-[2-(dimethylamino)-ethyl] -1H-indole-5-yl] -methyl} -2-oxazolidinone. The end compound is agonist of 5-HT₁-like receptors that are used effectively for treatment of patients suffering with migraine. EFFECT: improved method of synthesis, increased yield and purity of end product, simplified technology. 25 cl, 4 ex