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Synthesis of [guanido-13C]-γ-hydroxyarginine

✍ Scribed by Goo Yoon; T. Mark Zabriskie; Seung Hoon Cheon

Book ID
102371258
Publisher
John Wiley and Sons
Year
2009
Tongue
French
Weight
94 KB
Volume
52
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

This report describes an efficient method of synthesizing [guanido‐^13^C]‐γ‐hydroxyarginine HCl salt. Iodolactonization of N‐Boc‐protected allylglycine mainly provided the cis iodo compound 2. This was converted to an amine through azide 4. The amine 5 was reacted with N‐Boc‐protected [^13^C]thiourea to afford N‐Boc‐protected [^13^C]guanidine 6, which underwent base catalyzed ring opening. Removal of the N‐Boc group afforded [guanido‐^13^C]‐γ‐hydroxyarginine HCl salt 7 giving a 30% overall yield of the final product from N‐Boc protected allylglycine 1 in five steps. Copyright © 2008 John Wiley & Sons, Ltd.

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