Process for the preparation of (1S,4R)- or (1R,4S)-4-(2-amino-6- chloro-9H-purin-9-yl)-2-cyclo-pentene-1-methanol

Process for the preparation of (1S,4R)- or (1R,4S)-4-(2- amino-6-chloro-9H-purin-9-yl)-2-cyclo-pentene-1-methanol of the formulae (I) and (II) is described. This entails in the first stage (+/-)-2-aza-bicyclo[2.2.1]hept-5-en-3-one of the formula (III) being acylated to give a (+/-)-2-azabicyclo[2.2....

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Hauptverfasser:	BURGDORF KURT, ETTER KAY-SARA, BERNEGGER CHRISTINE, BRIEDEN WALTER, BOSSARD PIERRE, URBAN EVA MARIA, BIRCH OLWEN MARY, BRUX FRANK, GUGGISBERG YVES, DUC LAURENT, GORDON JOHN, O' MURCHU COLM
Format:	Patent
Sprache:	eng ; slo
Schlagworte:	ACYCLIC OR CARBOCYCLIC COMPOUNDS BEER BIOCHEMISTRY CHEMISTRY ENZYMOLOGY FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE HETEROCYCLIC COMPOUNDS METALLURGY MICROBIOLOGY MUTATION OR GENETIC ENGINEERING ORGANIC CHEMISTRY PROCESSES USING MICROORGANISMS SPIRITS VINEGAR WINE
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Zusammenfassung:	Process for the preparation of (1S,4R)- or (1R,4S)-4-(2- amino-6-chloro-9H-purin-9-yl)-2-cyclo-pentene-1-methanol of the formulae (I) and (II) is described. This entails in the first stage (+/-)-2-aza-bicyclo[2.2.1]hept-5-en-3-one of the formula (III) being acylated to give a (+/-)-2-azabicyclo[2.2.1]hept-5- en-3-one derivative of the general formula (IV) in which R1 denotes -(C1-C4)alkyl, -(C1-C4)alkoxy, aryl or aryloxy, the latter being reduced in the second stage to give a cyclopentene derivative of the general formula (V) in which R1 has the stated meaning, the latter then being converted in the third stage biotechnologically into the (1R,4S)- or (1S,4R)-1-amino-4- (hydroxymethyl)-2-cyclopentene of the formula (VI, VII) the latter being converted in the fourth stage with N-(2-amino-4,6- dichloro-5-pyrimidinyl)formamide of the formula (VIII) into the (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4- pyrimidinyl)amino]-2-cyclopentene-1-methanol of the formulae (IX, X) and the latter being cyclized in the fifth stage in a known manner to the final product of the formula (I) or (II). Opisuje sa spôsob výroby (1S,4R)- alebo (1R,4S)-4-(2-amino- 6-chlór-9-H-purín-9-yl)-2-cyklopentén-1-metanolu vzorcov (I) a (II). V prvom stupni sa acyluje (±)-2-azabicyklo[2.2.1]-hept-5- en-3-ón vzorca (III) na derivát (±)-2-azabicyklo[2.2.1]hept-5-en- 3-ónu všeobecného vzorca (IV), kde R1 znamená C1-4-alkyl, C1-4-alkoxy, aryl alebo aryloxy. Ten sa v druhom stupni redukuje na derivát cyklopenténu všeobecného vzorca (V), kde R1 má uvedený význam, ten sa v treťom stupni biotechnologicky premení na (1R,4S)- alebo (1S,4R)-1-amino-4-(hydroxymetyl)-2-cyklopentén vzorcov (VI), (VII). Ten sa v štvrtom stupni premení pomocou N-(2-amino-4,6-dichlórpyrimidín)-5-yl)formamidu vzorca (VIII) na (1S,4R)- alebo (1R,4S)-4-[(2-amino-6-chlór-5-formamido-4- pyrimidinyl)-amino]-2-cyklopentén-1-metanol vzorcov (IX), (X) a posledná menovaná zlúčenina sa v piatom stupni cyklizuje na konečný produkt vzorca (I) alebo (II).