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(Reference retrieved automatically from SciELO through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Continuous flow Aza-Michael reaction for preparing the fast-acting synthetic opioid drug Remifentanil

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Author(s):
Artur de Lara Lima Vaz [1] ; João Luis Callegari Lopes ; Giuliano Cesar Clososki [3]
Total Authors: 3
Affiliation:
[1] Universidade de São Paulo. Faculdade de Ciências Farmacêuticas de Ribeirão Preto. Departamento de Ciências BioMoleculares - Brasil
[3] Universidade de São Paulo. Faculdade de Ciências Farmacêuticas de Ribeirão Preto. Departamento de Ciências BioMoleculares - Brasil
Total Affiliations: 3
Document type: Journal article
Source: Brazilian Journal of Pharmaceutical Sciences; v. 59, 2023-06-16.
Abstract

Abstract Remifentanil is a modern fentanyl analogue with ultrashort-action granted by an esterase-labile methyl propanoate chain. Here, we present the development of a continuous flow methodology for the key N-alkylation step of remifentanil preparation in a biphasic, “slug-flow” regime. We screened parameters under microwave-assisted reactions, translated conditions to flow settings, and obtained remifentanil under 15-min residence time in a 1-mL microreactor, with a space-time yield of 89 mg/mL·h and 94% yield. (AU)

FAPESP's process: 22/05327-7 - Exploring the medicinal chemical space of aromatics with highly selective synthetic tools
Grantee:Giuliano Cesar Clososki
Support Opportunities: Regular Research Grants
FAPESP's process: 16/12718-1 - Application and development of continuous flow processes in the synthesis of fentanylic opioids
Grantee:Artur de Lara Lima Vaz
Support Opportunities: Scholarships in Brazil - Doctorate (Direct)