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Papers by Anna Balanov
Journal of Organic Chemistry, Dec 1, 1994
Thiol-mediated free radical cyclizations of but-3-enyl and but-3-ynyl isocyanides of types 6-8 gi... more Thiol-mediated free radical cyclizations of but-3-enyl and but-3-ynyl isocyanides of types 6-8 give new access to 3,5-disubstituted 2-(alkyl-and 2-(arylthio)pyrrolines 11, 12, and 18. When 2-mercaptoethanol is used with the same isocyanides the reaction results in pyroglutamates 16, 17, or 19. These cyclizations involve the formation of a new carbon-carbon bond through intramolecular addition of a carbon-centered thioimidoyl radical to a carbon-carbon multiple bond. Although cyclic products are usually obtained in high yields, in a few cases a competing radical degradation process leading to isothiocyanates was observed. Isocyanide Sa carrying an allyl-(phenyl) sulfide moiety isomerizes to 2-(phenylthio)pyrroline 24 in a series of sequential steps. Free radical reactions of isocyanides with thiols were reported by Saegusa and co-workers more than twenty years ago.' These authors observed that alkyl and phenyl isocyanides react with primary thiols yielding (alkylthiolformimidate, with tertiary thiols giving isothiocyanates, and with secondary thiols affording mixtures of thioformimidates and isothiocyanates. As delineated in eqs 1-4, addition of a thiyl radical to the isocyanide group ,S-R' R~-N=C.
Kluwer Academic Publishers eBooks, Dec 2, 2005
Organic Process Research & Development, Sep 13, 2021
La presente invention concerne de la rosuvastatine diastereomeriquement pure et des procedes d... more La presente invention concerne de la rosuvastatine diastereomeriquement pure et des procedes d'obtention de rosuvastatine diastereomeriquement pure ainsi que de ses intermediaires. Formule (I).
Le medicament Gabapentine enacarbil est synthetise et purifie a partir d'intermediaires comme... more Le medicament Gabapentine enacarbil est synthetise et purifie a partir d'intermediaires comme un carbamate ou carbonate de 1-halogenoalkyle et un squelette acetal de diacide. Par exemple, un carbonate ou carbamate de 1-halogenoalkyle est synthetise par combinaison d'un alcool en C 1 -C 10 ou d'une amine primaire en C 1 -C 10 , d'un solvant choisi dans le groupe constitue par : l'acetonitrile, les cetones en C 3 a C 7 , les ethers en C 5 a C 10 , les esters en C 2 a C 7 , les hydrocarbures en C 5 a C 10 et leurs melanges; d'un halogenoformate de 1-halogenoalkyle de formule suivante : (I) ou chacun des groupements X est independamment choisi parmi Br, I ou Cl; R 1 represente un groupement alkyle ou H; et d'une amine tertiaire en C 6 a C 21 .
La presente invention concerne la rosuvastatine, certains de ses intermediaires faiblement charge... more La presente invention concerne la rosuvastatine, certains de ses intermediaires faiblement charges en impuretes alkylether, et des procedes d'elaboration correspondants.
Organic Process Research & Development, 2021
La presente invention a pour objet des procedes et des intermediaires pour la preparation de rosu... more La presente invention a pour objet des procedes et des intermediaires pour la preparation de rosuvastatine.
An ether compound of formula I, having the structure: wherein R is a carboxyl protecting group th... more An ether compound of formula I, having the structure: wherein R is a carboxyl protecting group that is not methyl ester and R1 is a C1-C8 linear or branched.
Journal of Organic Chemistry, Dec 1, 1994
Thiol-mediated free radical cyclizations of but-3-enyl and but-3-ynyl isocyanides of types 6-8 gi... more Thiol-mediated free radical cyclizations of but-3-enyl and but-3-ynyl isocyanides of types 6-8 give new access to 3,5-disubstituted 2-(alkyl-and 2-(arylthio)pyrrolines 11, 12, and 18. When 2-mercaptoethanol is used with the same isocyanides the reaction results in pyroglutamates 16, 17, or 19. These cyclizations involve the formation of a new carbon-carbon bond through intramolecular addition of a carbon-centered thioimidoyl radical to a carbon-carbon multiple bond. Although cyclic products are usually obtained in high yields, in a few cases a competing radical degradation process leading to isothiocyanates was observed. Isocyanide Sa carrying an allyl-(phenyl) sulfide moiety isomerizes to 2-(phenylthio)pyrroline 24 in a series of sequential steps. Free radical reactions of isocyanides with thiols were reported by Saegusa and co-workers more than twenty years ago.' These authors observed that alkyl and phenyl isocyanides react with primary thiols yielding (alkylthiolformimidate, with tertiary thiols giving isothiocyanates, and with secondary thiols affording mixtures of thioformimidates and isothiocyanates. As delineated in eqs 1-4, addition of a thiyl radical to the isocyanide group ,S-R' R~-N=C.
Kluwer Academic Publishers eBooks, Dec 2, 2005
Organic Process Research & Development, Sep 13, 2021
La presente invention concerne de la rosuvastatine diastereomeriquement pure et des procedes d... more La presente invention concerne de la rosuvastatine diastereomeriquement pure et des procedes d'obtention de rosuvastatine diastereomeriquement pure ainsi que de ses intermediaires. Formule (I).
Le medicament Gabapentine enacarbil est synthetise et purifie a partir d'intermediaires comme... more Le medicament Gabapentine enacarbil est synthetise et purifie a partir d'intermediaires comme un carbamate ou carbonate de 1-halogenoalkyle et un squelette acetal de diacide. Par exemple, un carbonate ou carbamate de 1-halogenoalkyle est synthetise par combinaison d'un alcool en C 1 -C 10 ou d'une amine primaire en C 1 -C 10 , d'un solvant choisi dans le groupe constitue par : l'acetonitrile, les cetones en C 3 a C 7 , les ethers en C 5 a C 10 , les esters en C 2 a C 7 , les hydrocarbures en C 5 a C 10 et leurs melanges; d'un halogenoformate de 1-halogenoalkyle de formule suivante : (I) ou chacun des groupements X est independamment choisi parmi Br, I ou Cl; R 1 represente un groupement alkyle ou H; et d'une amine tertiaire en C 6 a C 21 .
La presente invention concerne la rosuvastatine, certains de ses intermediaires faiblement charge... more La presente invention concerne la rosuvastatine, certains de ses intermediaires faiblement charges en impuretes alkylether, et des procedes d'elaboration correspondants.
Organic Process Research & Development, 2021
La presente invention a pour objet des procedes et des intermediaires pour la preparation de rosu... more La presente invention a pour objet des procedes et des intermediaires pour la preparation de rosuvastatine.
An ether compound of formula I, having the structure: wherein R is a carboxyl protecting group th... more An ether compound of formula I, having the structure: wherein R is a carboxyl protecting group that is not methyl ester and R1 is a C1-C8 linear or branched.