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Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist

✍ Scribed by John Y.L Chung; Guo-Jie Ho; Michel Chartrain; Chris Roberge; Dalian Zhao; John Leazer; Roger Farr; Michael Robbins; Kateeta Emerson; David J Mathre; James M McNamara; David L Hughes; Edward J.J Grabowski; Paul J Reider

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
293 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

A chemoenzymatic synthesis of 133 agonist 1 suitable for large scale preparation is described. The key chiral 3pyridylethanolamine 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.

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Convergent synthesis of two 14C-labeled
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The synthesis of b 3 -adrenergic receptor agonists A and B with radiolabeled amide fragment, required for drug disposition studies, was accomplished based on initial formation of 2-(4-(2-amino-2-methylpropyl)phenoxy)-5-[ 14 C]-cyanopyridine by the reaction of 2-bromo-5-iodopyridine with para-substit