𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Cu(I)Br-mediated preparation of 14C-labeled 3-pyridineacetate derivatives and synthesis of a novel 14C-labeled PDE-IV inhibitor

✍ Scribed by Jonathan Z. Ho; Matthew P. Braun

Publisher
John Wiley and Sons
Year
2007
Tongue
French
Weight
99 KB
Volume
50
Category
Article
ISSN
0022-2135

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

An efficient protocol for the synthesis of ^14^C‐labeled 3‐pyridineacetate (1) and its N‐oxide ([^14^C]2) is described. Oxidation of this pyridine ([^14^C]1) to its N‐oxide ([^14^C]2) proceeded in high yield using H~2~O~2~ with MeReO~3~ as a catalyst. The reaction employs readily available diethyl [2‐^14^C]malonate. This method has proven to be general in preparation of other pyridineacetate derivatives and their N‐oxides which have been typically difficult to prepare by other means. Our development of the Cu(I)Br‐coupling methodology as well as application to the synthesis of a ^14^C‐labeled phosphodiesterase‐IV (PDE‐IV) inhibitor, [^14^C]3, are also reported. Copyright © 2007 John Wiley & Sons, Ltd.

📜 SIMILAR VOLUMES

Use of Dibutyl[14C]formamide as a Formyl
Use of Dibutyl[14C]formamide as a Formylating Reagent in the Vilsmeier–Haack Reaction and Synthesis of a 14C-Labeled Novel Phosphodiesterase-4 (PDE-4) Inhibitor
✍ Jonathan Z. Ho; Charles S. Elmore; Michael A. Wallace; Dan Yao; Matthew P. Braun 📂 Article 📅 2005 🏛 John Wiley and Sons 🌐 German ⚖ 204 KB

## Abstract A simple, high‐yielding synthesis of dibutyl[^14^C]formamide ([^14^C]DBF; **1**) from ^14^CO~2~ was developed (__Scheme 1__): reaction of LiBEt~3~H and ^14^CO~2~ followed by aqueous workup gave H^14^CO~2~H in high yield. Conversion of the [^14^C]formic acid to **1** was effected by a st

Synthesis of a labeled inhibitor of HIV-
Synthesis of a labeled inhibitor of HIV-1 attachment: 1-(4-benzoylpiperazin-1-yl)-2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridinyl-3-yl-[U-14C]ethane-1,2-dione, BMS-488043-14C
✍ I. Victor Ekhato; J. Kent Rinehart 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 French ⚖ 118 KB

## Abstract BMS‐488043 is a potent inhibitor of the interaction between HIV‐1 gp120 and the host cell receptor CD4. We prepared the carbon‐14‐labeled version to support preclinical studies of the compound. It was prepared from ethyl [U‐^14^C]oxalyl chloride by a sequence using Friedel–Crafts acylat

14C-labeling of a novel fungicide. I. Sy
14C-labeling of a novel fungicide. I. Syntheses of optically active (E)-and (Z)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-[14C]-1-YL)-1-penten-3-OLS
✍ Iwao Nakatsuka; Hiroshi Kanamaru; Takeshi Kamada; Kazuo Kawahara; Akira Yoshitak 📂 Article 📅 1986 🏛 John Wiley and Sons 🌐 French ⚖ 384 KB

A novel fungicide, (-) (E)-1-( 2,4-di chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol (S-3308 L) and i t s three o p t i c a l l y active stereoisaners were labeled w i t h carbon-14 a t the t r i a z o l e r i n g f o r use i n the metabolic and environmental f a t e studies. 1 ,2,