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Synthesis 2007(13): 1927-1929  
DOI: 10.1055/s-2007-983721
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of the Immunomodulating Compound KRP-203

Maiko Hamada*, Masatoshi Kiuchi, Kunitomo Adachi
Chemistry Laboratory Pharmaceuticals Research Division, Mitsubishi Pharma Corporation, 1000, Kamoshida-cho, Aoba-ku, Yokohama, Kanagawa 227-0033, Japan
Fax: +81(45)9633529; e-Mail: Hamada.Maiko@mc.m-pharma.co.jp;
Further Information

Publication History

Received 6 March 2007
Publication Date:
18 June 2007 (online)

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Abstract

A practical and concise synthesis of KRP-203 (1) was achieved by utilizing a palladium coupling reaction mediated by XantPhos and Pd2(dba)3 as the key step. The coupling reaction of aryl bromide 5 with 3-hydroxythiophenol (6) proceeded chemoselectively to give phenol 7 in spite of the presence of a chlorine substituent on 5 and a hydroxyl group on 6. Phenol 7 was converted into KRP-203 by benzylation and removal of the protecting groups in high yield.

Key words

palladium - cross-coupling - synthesis - KRP-203 - FTY720

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