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Synlett 2014; 25(2): 265-269
DOI: 10.1055/s-0033-1340281
DOI: 10.1055/s-0033-1340281
letter
An Alternate Synthesis of Bosentan Monohydrate, an Endothelin Receptor Antagonist[1]
Further Information
Publication History
Received: 16 August 2013
Accepted after revision: 14 October 2013
Publication Date:
02 December 2013 (online)
![](https://www.thieme-connect.de/media/synlett/201402/lookinside/thumbnails/10.1055-s-0033-1340281-1.jpg)
Abstract
An alternate synthesis of an endothelin receptor antagonist bosentan monohydrate is reported. This new synthetic route involves the coupling of p-tert-butyl-N-[6-chloro-5-(2-methoxy-phenoxy)(2,2′-bipyrimidin)-4-yl]benzene sulfonamide with commercially available raw material (2,2-dimethyl-1,3-dioxolan-4-yl)methanol as the key step. Attractive features of this approach are its versatileness, commercial availability of raw materials, usage of eco-friendly reagents, and it efficiently provides the desired bosentan monohydrate free from reported impurities such as dimer, N-alkylated, and pyrimidinone impurities.
Key words
alternate synthesis - bosentan monohydrate - eco-friendly reagents - dimer impurity - N-alkylated - pyrimidinoneSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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References and Notes
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- 13 HPLC Method Column: BDS Hypersil C18, 250 × 4.6 mm, 5 μm; UV, λ = 220 nm; temp: 30 °C; load: 20 μL; elution: gradient; buffer: dipotassium hydrogen orthophosphate; diluent: mobile phase A + mobile phase-B; mobile phase A: 95% buffer + 5% MeOH; mobile phase B: 95% MeOH + 5% H2O.
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