Practical [14C]-synthesis of molecules containing an acetic acid moiety: application to [14C]-labeled DP1 antagonists

✍ Scribed by Carl Berthelette; Zhaoyin Wang

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: French
• Weight: 104 KB
• Volume: 50
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.1146

✦ Synopsis

Abstract

Efficient carbon‐14 labeling of four potent and selective DP1 antagonists is reported. The synthetic sequence began with α‐hydroxylation, reduction of an ester, followed by oxidative diol cleavage and aldehyde reduction. The resulting alcohol 4 was converted to a mesylate then nucleophilic substitution with [^14^C]‐sodium cyanide was performed to yield a nitrile, which upon basic hydrolysis provided the carbon‐14 labeled acid 1. Compound 2 was obtained from the same alcohol intermediate 4 and two diastereomeric compounds 6 and 7 were easily prepared from compound 2. Carbon‐14 synthesis of compounds 1, 2, 6 and 7 were achieved in good yields, high radiochemical purity (>99%) and with high specific activity (45 mCi/mmol). Copyright © 2006 John Wiley & Sons, Ltd.