Guided optimization of a crystallization-induced diastereomer transformation to access a key navoximod intermediate-Reference-Cited by-同舟云学术

Guided optimization of a crystallization-induced diastereomer transformation to access a key navoximod intermediate

Published:2023 Issue:6 Volume:8 Page:1294-1299
ISSN:2058-9883
Container-title:Reaction Chemistry & Engineering
language:en
Short-container-title:React. Chem. Eng.

Author:

Kukor Andrew J.¹,St-Jean Frédéric²^ORCID,Stumpf Andreas²,Malig Thomas C.³,Piechowicz Katarzyna A.²,Kurita Kenji³^ORCID,Hein Jason E.¹^ORCID

Affiliation:

1. Department of Chemistry, The University of British Columbia, Vancouver, BC, V6T 1Z1, Canada

2. Department of Small Molecule Process Chemistry, Genentech, Inc., South San Francisco, California, 94080, USA

3. Department of Small Molecule Analytical Chemistry Quality Control, Genentech, Inc., South San Francisco, California, 94080, USA

Abstract

The crystallization-induced diastereomer transformation of a precursor to navoximod was investigated using online HPLC and optimized with inline racemization.

Funder

Natural Sciences and Engineering Research Council of Canada

Genentech

Canada Foundation for Innovation

University of British Columbia

Publisher

Royal Society of Chemistry (RSC)

Subject

Fluid Flow and Transfer Processes,Process Chemistry and Technology,Chemical Engineering (miscellaneous),Chemistry (miscellaneous),Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2023/RE/D3RE00077J

Reference21 articles.

1. Why tumours eat tryptophan

2. An endogenous tumour-promoting ligand of the human aryl hydrocarbon receptor

3. Phase I Study of the Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitor Navoximod (GDC-0919) Administered with PD-L1 Inhibitor (Atezolizumab) in Advanced Solid Tumors

4. Stereoselective Synthesis of the IDO Inhibitor Navoximod

5. Crystallization-Induced Diastereomer Transformations

Cited by 5 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Investigating the Origin of Epimerization Attenuation during Pd-Catalyzed Cross-Coupling Reactions;ACS Catalysis;2024-08-03

2. Crystallization-Induced Diastereomeric Transformation of Chiral Ozanimod Key Intermediate Using Homogeneous Ir-Based Racemization Catalyst;Crystal Growth & Design;2024-06-11

3. Semicontinuous Temperature Cycle-Induced Deracemization Using an Axially Chiral Naphthamide;Organic Process Research & Development;2024-04-30

4. Practical Manufacturing Process for Baloxavir Marboxil: Effective Selection and Replacement of Protective Group toward Enhancement of Crystallization-Induced Diastereomer Transformation;Organic Process Research & Development;2024-04-04

5. Stereochemical Editing via Coupled Epimerization and Optical Resolution to Sustainably Manufacture a Key Adagrasib Building Block;Organic Process Research & Development;2023-11-30