Mixed anhydrides: physical properties influenced by molecular structure

Penn, John H.; Owens, Walter H.; Petersen, Jeffrey L.; Finklea, Harry O.; Snider, Daniel A.

doi:10.1021/jo00060a032

Cited by 7 publications

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“…First, since trifluoroacetic anhydride (TFAA) is a known potential impurity present in TFA, it was envisioned that the reaction of TFAA and compound 6 could be the source of impurity 14 (Scheme , TFAA pathway). Alternatively, a reaction between acryloyl chloride and TFA may generate a mixed anhydride, which subsequently reacts with compound 6 to afford impurity 14 (Scheme , mixed anhydride pathway). A series of control experiments were performed to identify the operative pathway, with the results summarized in Table .…”

Section: Resultsmentioning

confidence: 99%

Development of a Commercial Manufacturing Process for Sotorasib, a First-in-Class KRAS^G12C Inhibitor

Zhang

Griffin

Beaver

et al. 2022

Org. Process Res. Dev.

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A commercial process to manufacture sotorasib (AMG 510), a first-in-class KRASG12C inhibitor, is described. Development efforts focused on rendering a fit-for-purpose early-phase route into a viable long-term commercial process through the reduction of side reactions to improve yield and product quality, as well as reducing cycle times of crystallization processes by improving particle properties and filtration times. These improvements were key to ensuring clinical supply and commercial launch. The final route consists of five synthetic operations from starting material M-1, including a telescoped two-step sequence, and a final form-setting crystallization.

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Section: Resultsmentioning

confidence: 99%

Development of a Commercial Manufacturing Process for Sotorasib, a First-in-Class KRAS^G12C Inhibitor

Zhang

Griffin

Beaver

et al. 2022

Org. Process Res. Dev.

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Understanding α-amino acid chemistry from X-ray diffraction structures

1996

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Inverconversion of Nitriles, Carboxylic Acids, and Derivatives

Larock

Rozhkov

2018

Comprehensive Organic Transformations

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Carboxylic Acids to Acid Halides Carboxylic Acids to Acid Anhydrides Carboxylic Acids to Esters Carboxylic Acids to Amides Carboxylic Acids to Imides Carboxylic Acids to Nitriles Acid Halides to Other Acid Halides Acid Halides to Acid Anhydrides Acid Halides to Esters Acid Halides to Amides Acid Halides to Imides Acid Halides to Nitriles Acid Anhydrides to Acid Halides Acid Anhydrides to Esters Acid Anhydrides to Amides Acid Anhydrides to Imides Esters to Carboxylic Acids Esters to Acid Halides Esters to Acid Anhydrides Esters to Other Esters Esters to Amides Esters to Nitriles Amides to Carboxylic Acids Amides to Esters Amides to Other Amides Amides to Imides Amides to Nitriles Imides to Esters or Lactones Imides to Amides Imides to Other Imides Nitriles to Carboxylic Acids Nitriles to Esters Nitriles to Amides Other Interconversions

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Mixed anhydrides: physical properties influenced by molecular structure

Cited by 7 publications

References 0 publications

Development of a Commercial Manufacturing Process for Sotorasib, a First-in-Class KRAS^G12C Inhibitor

Development of a Commercial Manufacturing Process for Sotorasib, a First-in-Class KRAS^G12C Inhibitor

Understanding α-amino acid chemistry from X-ray diffraction structures

Inverconversion of Nitriles, Carboxylic Acids, and Derivatives

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Mixed anhydrides: physical properties influenced by molecular structure

Cited by 7 publications

References 0 publications

Development of a Commercial Manufacturing Process for Sotorasib, a First-in-Class KRASG12C Inhibitor

Development of a Commercial Manufacturing Process for Sotorasib, a First-in-Class KRASG12C Inhibitor

Understanding α-amino acid chemistry from X-ray diffraction structures

Inverconversion of Nitriles, Carboxylic Acids, and Derivatives

Contact Info

Product

Resources

About

Development of a Commercial Manufacturing Process for Sotorasib, a First-in-Class KRAS^G12C Inhibitor

Development of a Commercial Manufacturing Process for Sotorasib, a First-in-Class KRAS^G12C Inhibitor