Practical enantioselective synthesis of a COX-2 specific inhibitor

Lushi Tan; Cheng Yi Chen; Weirong Chen; Lisa Frey; Anthony O. King; Richard D. Tillyer; Feng Xu; Dalian Zhao; Edward J.J. Grabowski; Paul J. Reider; Paul O'Shea; Philippe Dagneau; Xin Wang

doi:10.1016/S0040-4020(02)00826-8

Practical enantioselective synthesis of a COX-2 specific inhibitor

Lushi Tan, Cheng Yi Chen, Weirong Chen, Lisa Frey, Anthony O. King, Richard D. Tillyer, Feng Xu, Dalian Zhao, Edward J.J. Grabowski, Paul J. Reider, Paul O'Shea, Philippe Dagneau, Xin Wang

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

20 Scopus citations

Abstract

Two synthetic strategies to the COX-2 specific inhibitor 1 have been described that allowed its preparation in large quantities in 79% overall yield from (S)-2-hydroxy-2-methylbutyric acid. These studies have led to the identification of an efficient resolution of (±)-2-hydroxy-2-methylbutyric acid and a novel thionyl chloride aided formation of amide 11 from acid 6.

Original language	English (US)
Pages (from-to)	7403-7410
Number of pages	8
Journal	Tetrahedron
Volume	58
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4020(02)00826-8
State	Published - Sep 9 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

COX-2 inhibitor
Hydroxy ketone
Resolution
Suzuki coupling

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10.1016/S0040-4020(02)00826-8

Cite this

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title = "Practical enantioselective synthesis of a COX-2 specific inhibitor",

abstract = "Two synthetic strategies to the COX-2 specific inhibitor 1 have been described that allowed its preparation in large quantities in 79% overall yield from (S)-2-hydroxy-2-methylbutyric acid. These studies have led to the identification of an efficient resolution of (±)-2-hydroxy-2-methylbutyric acid and a novel thionyl chloride aided formation of amide 11 from acid 6.",

keywords = "COX-2 inhibitor, Hydroxy ketone, Resolution, Suzuki coupling",

author = "Lushi Tan and Chen, {Cheng Yi} and Weirong Chen and Lisa Frey and King, {Anthony O.} and Tillyer, {Richard D.} and Feng Xu and Dalian Zhao and Grabowski, {Edward J.J.} and Reider, {Paul J.} and Paul O'Shea and Philippe Dagneau and Xin Wang",

year = "2002",

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doi = "10.1016/S0040-4020(02)00826-8",

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T1 - Practical enantioselective synthesis of a COX-2 specific inhibitor

AU - Tan, Lushi

AU - Chen, Cheng Yi

AU - Chen, Weirong

AU - Frey, Lisa

AU - King, Anthony O.

AU - Tillyer, Richard D.

AU - Xu, Feng

AU - Zhao, Dalian

AU - Grabowski, Edward J.J.

AU - Reider, Paul J.

AU - O'Shea, Paul

AU - Dagneau, Philippe

AU - Wang, Xin

PY - 2002/9/9

Y1 - 2002/9/9

N2 - Two synthetic strategies to the COX-2 specific inhibitor 1 have been described that allowed its preparation in large quantities in 79% overall yield from (S)-2-hydroxy-2-methylbutyric acid. These studies have led to the identification of an efficient resolution of (±)-2-hydroxy-2-methylbutyric acid and a novel thionyl chloride aided formation of amide 11 from acid 6.

AB - Two synthetic strategies to the COX-2 specific inhibitor 1 have been described that allowed its preparation in large quantities in 79% overall yield from (S)-2-hydroxy-2-methylbutyric acid. These studies have led to the identification of an efficient resolution of (±)-2-hydroxy-2-methylbutyric acid and a novel thionyl chloride aided formation of amide 11 from acid 6.

KW - COX-2 inhibitor

KW - Hydroxy ketone

KW - Resolution

KW - Suzuki coupling

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U2 - 10.1016/S0040-4020(02)00826-8

DO - 10.1016/S0040-4020(02)00826-8

M3 - Article

AN - SCOPUS:18644383018

SN - 0040-4020

VL - 58

SP - 7403

EP - 7410

JO - Tetrahedron

JF - Tetrahedron

IS - 37

ER -

Practical enantioselective synthesis of a COX-2 specific inhibitor

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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