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Cas No. 494224-44-1, tert-butyl(4-(3-(dimethoxyphosphoryl)-2-oxopropyl)phenyl)carbamate

  • 494224-44-1

  • C16H24NO6P

  • 357.34

  • 1.212±0.06

  • 98% min (HPLC)

  • Overactive Bladder

  • Vibegron

  • 12/1/2030 (Vibegron)

  • beta-3 adrenergic receptor

  • N

  • ISO 9001;ISO 14001;ISO 45001; GMP

Availability:

DESCRIPTION

By selectively targeting the β3-adrenergic receptor, Vibegron exhibits superior efficacy and tolerability compared to traditional OAB medications. With its rapid onset and prolonged duration, Vibegron empowers patients and healthcare providers to manage OAB symptoms with a simplified and effective approach. By integrating Vibegron into your pharmaceutical portfolio, you can expand your impact on patients' quality of life and establish a new standard of care in OAB treatment.

ROS

The predominant components of Vibegron, the pyrrolidine imine part with three chiral centers (A), and the pyrrolopyrimidine part with one chiral center(B), are synthesized from specific compounds.


Final steps of Vibegron synthesis


The pyrrolidine imine part (A) is derived from the compound with CAS RN 1295539-30-8, or its Boc-protected alternative, CAS RN 1190391-85-5. Whereas, the pyrrolopyrimidine part (B) can take various acid forms of the compound with CAS RN 1190392-22-3 or its sodium salt equivalent with CAS RN 1421271-01-3, such as hydrochloride acid, tartaric acid, malic acid, mandelic acid, and maleic acid.


The selection of the sodium salt may require additional acid to extract the pyrrolopyrimidine moiety, potentially adding complexity to your manufacturing process. However, choosing the acid salt forms omits the need for additional acid during handling, thereby easing the route towards commercialization of Vibegron.




What is the compound CAS RN 494224-44-1 role?


The current compound 494224-44-1 can be used to synthesize the pyrroidine imine part (A). For instance, in the overall synthesis map of Vibegron (feel free to download it), this compound is reacted with the compound whose CAS RN is 163625-46-5, followed by hydrogenation using Pd/C catalyst. 


Use of 494224-44-1 in Vibegron Synthesis


References

吕宏海, 郭万成, 房杰, 王国平 & 于振鹏. 一种维贝格龙中间体及其制备方法. (2023).


Berger, R. et al. Hydroxymethyl pyrrolidines as beta 3 adrenergic receptor agonists. (2009).


Nagabukuro, H., Edmondson, S. D., Sinharoy, M. S., Denney, W. S. & Frenkl, T. L. Combination therapy using a beta 3 adrenergic receptor agonist and an antimuscarinic agent. (2011).


Xu, F. et al. Synthesis of Vibegron Enabled by a Ketoreductase Rationally Designed for High pH Dynamic Kinetic Reduction. Angew Chem Int Ed 57, 6863–6867 (2018).


Yasuda, N. et al. Process for making beta 3 agonists and intermediates. (2013).


US20090253705A1 - Hydroxymethyl pyrrolidines as beta 3 adrenergic receptor agonists



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