Stereoretentive Etherification of an α-Aryl-ß-amino Alcohol Using a Selective Aziridinium Ring Opening for the Synthesis of AZD7594.
J Org Chem
; 84(8): 4629-4638, 2019 04 19.
Article
em En
| MEDLINE
| ID: mdl-29920203
ABSTRACT
A selective aziridinium ring-opening was used to etherify an α-aryl-ß-amino alcohol with stereochemical retention. This transformation was achieved in a biphasic system to address phenoxide solubility and the formation of a sulfonate ester impurity. The protecting group strategy was directed by a stability study of the activated α-aryl-ß-amino alcohol in this system. Process analytical techniques were used to establish reaction understanding, and mixing on large scale was modeled in silico. The process provided a selective and efficient method of preparing the nonsteroidal, inhaled selective glucocorticoid receptor modulator AZD7594.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Aziridinas
/
Dioxinas
/
Ésteres
/
Furanos
/
Amino Álcoois
/
Indazóis
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article