Efficient and facile synthesis of novel stable monodeuterium labeled ractopamine

Su, Feifei; Wu, Fulong; Tang, He; Wang, Zhonghua; Wu, Fanhong

doi:10.1002/jlcr.3355

Cited by 4 publications

(2 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Subsequently, Wang and his colleagues applied simple phenyl aldehyde as raw material to obtain deuterated ractopamine via reduction, protection, sub-stitution, coupling, and deprotection sequence in 9 steps with 44 % total yields (Scheme 1c). [20] However, by using this protocol, only one atom was labeled, which is + 1 m/z away from the naturally abundant ractopamine. Therefore, this approach has obvious limitations in practical application.…”

Section: Introductionmentioning

confidence: 99%

“…However, these protocols all use expensive deuterated reagents with long synthetic routes, complex operations and low yields. Subsequently, Wang and his colleagues applied simple phenyl aldehyde as raw material to obtain deuterated ractopamine via reduction, protection, substitution, coupling, and deprotection sequence in 9 steps with 44 % total yields (Scheme 1c) [20] . However, by using this protocol, only one atom was labeled, which is +1 m/z away from the naturally abundant ractopamine.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Efficient Synthesis of Ractopamine‐D₃ via Epoxide‐Opening Strategy

Wang,

Wu,

Chen

et al. 2023

Asian J Org Chem

View full text Add to dashboard Cite

The incorporation of deuterium isotopes into illicit additives like ractopamine holds significant promise for enabling swift and accurate detection. However, current synthetic methodologies for deuterium labeling often involve intricate and time‐consuming processes, necessitating laborious de/protection steps and specialized equipment. Herein, after establishing efficient epoxide‐opening reactions using diverse primary amines, a practical, efficient and straightforward synthetic route for producing deuterium‐labeled ractopamine‐D3 has been successfully established, which was confirmed by 1H‐NMR and ESI‐MS with a deuterium isotope abundance exceeding 98 atom% D. Remarkably, this newly devised convergent synthetic protocol, encompassing just three steps, delivered up to 53% overall yield of ractopamine‐D3, underscoring its scalability and potential pharmaceutical viability.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Ractopamine‐D₃ via Epoxide‐Opening Strategy

Wang,

Wu,

Chen

et al. 2023

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

Development and Scale-Up of Stereoretentive α-Deuteration of Amines

Michelotti¹,

Rodrigues²,

Roche³

2017

Org. Process Res. Dev.

View full text Add to dashboard Cite

A stereoretentive deuteration of amino acids and amines has been developed using ruthenium on carbon catalyst, hydrogen gas at atmospheric pressure, and deuterium oxide as a source of deuterium. The process was successfully scaled-up, avoiding the use of expensive and sensitive catalyst and avoiding the use of deuterium gas under pressure. High deuterium incorporation and high yield of labeled compounds were obtained by a simple filtration process.

show abstract