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

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

doi:10.1016/S0040-4039(99)01353-2

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

John Y.L. Chung, Guo Jie Ho, Michel Chartrain, Chris Roberge, Dalian Zhao, John Leazer, Roger Farr, Micheal Robbins, Kateeta Emerson, David J. Mathre, James M. McNamara, David L. Hughes, Edward J.J. Grabowski, Paul J. Reider

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38 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	6739-6743
Number of pages	5
Journal	Tetrahedron Letters
Volume	40
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4039(99)01353-2
State	Published - Sep 10 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)01353-2

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Chung, J. Y. L., Ho, G. J., Chartrain, M., Roberge, C., Zhao, D., Leazer, J., Farr, R., Robbins, M., Emerson, K., Mathre, D. J., McNamara, J. M., Hughes, D. L., Grabowski, E. J. J., & Reider, P. J. (1999). Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β₃ adrenergic receptor agonist. Tetrahedron Letters, 40(37), 6739-6743. https://doi.org/10.1016/S0040-4039(99)01353-2

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abstract = "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.",

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T1 - Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist

AU - Chung, John Y.L.

AU - Ho, Guo Jie

AU - Chartrain, Michel

AU - Roberge, Chris

AU - Zhao, Dalian

AU - Leazer, John

AU - Farr, Roger

AU - Robbins, Micheal

AU - Emerson, Kateeta

AU - Mathre, David J.

AU - McNamara, James M.

AU - Hughes, David L.

AU - Grabowski, Edward J.J.

AU - Reider, Paul J.

PY - 1999/9/10

Y1 - 1999/9/10

N2 - 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.

AB - 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.

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M3 - Article

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SN - 0040-4039

VL - 40

SP - 6739

EP - 6743

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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