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",

month = sep,

day = "9",

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

language = "English (US)",

volume = "58",

pages = "7403--7410",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "37",

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TY - JOUR

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

UR - https://www.scopus.com/pages/publications/18644383018

UR - https://www.scopus.com/pages/publications/18644383018#tab=citedBy

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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