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

Research output: Contribution to journal › Article › peer-review

43 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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title = "Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist",

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.",

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

year = "1999",

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doi = "10.1016/S0040-4039(99)01353-2",

language = "English (US)",

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pages = "6739--6743",

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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.

UR - https://www.scopus.com/pages/publications/0033543625

UR - https://www.scopus.com/pages/publications/0033543625#tab=citedBy

U2 - 10.1016/S0040-4039(99)01353-2

DO - 10.1016/S0040-4039(99)01353-2

M3 - Article

AN - SCOPUS:0033543625

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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