Synthesis of carbon-14 labelled CD 271 (6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid) a potential new agent for dermatology
✍ Scribed by W. R. Pilgrim; P. Nedoncelle; J-P. Frideling; B. Shroot
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- French
- Weight
- 290 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
6‐[3‐(1‐Adamantyl)‐4‐methoxyphenyl]‐2‐naphthoic acid (1), a promising new compound for the treatment of disorders of keratinization, has been synthesized in [^14^C]‐labelled form from barium [^14^C]‐carbonate via labelled benzene. Benzene‐[U‐^14^C] was converted to 4‐bromo‐methoxybenzene‐[phenyl‐U‐^14^C] in six steps. Introduction of the adamantyl ring was carried out using 1‐acetoxyadamantane under acid catalysis. 2‐(1‐Adamantyl)‐4‐bromo‐methoxybenzene‐[phenyl‐U‐^14^C] (2) was converted to a zincate and coupled with methyl 6‐bromo‐2‐naphthoate using a nickel catalyst. The product of the aryl coupling reaction (3) was then saponified to give 6‐[3‐(1‐adamantyl)‐4‐methoxyphenyl‐[phenyl‐U‐^14^C]]‐2‐naphthoic acid.