Br COзн Et,N DBU CH;SO2 phenylacetic acid CH;SO2 х rofecoxib

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter21: Lipids
Section: Chapter Questions
Problem 21.63P
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Reaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal antiinflammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxib.

Br
COзн
Et,N
DBU
CH;SO2
phenylacetic acid
CH;SO2
х
rofecoxib
Transcribed Image Text:Br COзн Et,N DBU CH;SO2 phenylacetic acid CH;SO2 х rofecoxib
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