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Scalable synthesis of a prostaglandin EP4 receptor antagonist.
Gauvreau, Danny; Dolman, Sarah J; Hughes, Greg; O'Shea, Paul D; Davies, Ian W.
Afiliação
  • Gauvreau D; Department of Process Research, Merck Frosst Centre for Therapeutic Research, 16711 Trans Canada Hwy, Kirkland, Québec, Canada H9H 3L1. danny_gauvreau@merck.com
J Org Chem ; 75(12): 4078-85, 2010 Jun 18.
Article em En | MEDLINE | ID: mdl-20469914
The evolution of scalable, economically viable synthetic approaches to the potent and selective prostaglandin EP4 antagonist 1 is presented. The chromatography-free synthesis of multikilogram quantities of 1 using a seven-step sequence (six in the longest linear sequence) is described. This approach has been further modified in an effort to identify a long-term manufacturing route. Our final synthesis involves no step requiring cryogenic (< -25 degrees C) conditions; comprises a total of four steps, only three of which are in the longest linear synthesis; and features the use of two consecutive iron-catalyzed Friedel-Crafts substitutions.
Assuntos

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Química Farmacêutica / Receptores de Prostaglandina E Idioma: En Revista: J Org Chem Ano de publicação: 2010 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Química Farmacêutica / Receptores de Prostaglandina E Idioma: En Revista: J Org Chem Ano de publicação: 2010 Tipo de documento: Article