Axial Chirality in the Sotorasib Drug Substance, Part 2: Leveraging a High-Temperature Thermal Racemization to Recycle the Classical Resolution Waste Stream-Reference-Cited by-同舟云学术

Axial Chirality in the Sotorasib Drug Substance, Part 2: Leveraging a High-Temperature Thermal Racemization to Recycle the Classical Resolution Waste Stream

Published:2022-08-23 Issue:9 Volume:26 Page:2636-2645
ISSN:1083-6160
Container-title:Organic Process Research & Development
language:en
Short-container-title:Org. Process Res. Dev.

Author:

Beaver Matthew G.¹^ORCID,Brown Derek B.²^ORCID,Campbell Kiersten³,Fang Yuan-Qing³^ORCID,Ford David D.³^ORCID,Mardirossian Narbe⁴,Nagy Kevin D.³,Rötheli Andreas R.¹^ORCID,Sheeran Jillian W.³,Telmesani Reem³,Parsons Andrew T.¹^ORCID

Affiliation:

1. Process Development, Amgen, Inc., 360 Binney Street, Cambridge, Massachusetts 02142, United States

2. Pivotal and Commercial Synthetics, Amgen, Inc., One Amgen Center Drive, Thousand Oaks, California 91320, United States

3. Snapdragon Chemistry, 300 2nd Avenue, Waltham, Massachusetts 02451, United States

4. Molecular Engineering, Amgen, Inc., One Amgen Center Drive, Thousand Oaks, California 91320, United States

Funder

Amgen

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/acs.oprd.2c00177

Reference21 articles.

1. Green Chemistry as a Driver for Innovation in the Pharmaceutical Industry

2. Thermal racemization of biaryl atropisomers

3. Numerous basic and acidic additives were investigated to lower the activation barrier of racemization. Significant decomposition was observed in all cases, with negligible improvement in racemization rate.

4. P-1 and M-1 were used interchangeably through these initial studies based on material availability.

5. The rate constant for the desired forward reaction equals slope/2 for a first-order reversible reaction where k1 = k–1.

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