107445-24-9Relevant articles and documents
Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist
Chung, John Y. L.,Ho, Guo-Jie,Chartrain, Michel,Roberge, Chris,Zhao, Dalian,Leazer, John,Farr, Roger,Robbins, Micheal,Emerson, Kateeta,Mathre, David J.,McNamara, James M.,Hughes, David L.,Grabowski, Edward J. J.,Reider, Paul J.
, p. 6739 - 6743 (2007/10/03)
A chemoenzymatic synthesis of β3 agonist 1 suitable for large scale preparation is described. The key chiral 3-pyridylethanolamine intermediate (R)-7 was prepared via an improved Neber rearrangement and a yeast-mediated asymmetric reduction. The tetrazolone fragment of the molecule was constructed via a dipolar cycloaddition between 1-(cyclopentyl)-3-propylazide and p-chlorosulfonyl phenylisocyanate. Sulfonamide coupling of these two intermediates under Shotten-Baumann conditions, followed by a borane reduction of the amide afforded 1 in 20-32% overall yield from 3-acetylpyridine.