E. Azim, J. M. Dupuy, J. Maurizis
Jul 1, 1997
Citations
0
Influential Citations
5
Citations
Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
Carbonation of CH 3 MgI with 14 CO 2 led to sodium [1- 14 C] acetate: 1 which was successively brominated and esterifed with diazomethane to give rise to methyl 2-bromo-[-1- 14 C] acetate: 3, the reduction of which with H 3 Al gave 2-bromo-[-1- 14 C] ethanol 4. 4 was then reacted with NaCN; the intermediate 3-hydroxy-[-3- 14 C] propionitrile 5 was hydrolyzed with HCI at 130°C into the corresponding acid: 6 which was transformed into 3-chloro-[-3- 14 C] propionyl chloride: 7 ; 7 reacted with NaN 3 gave 3- chloro-[-3- 14 C] propyl azide: 8 which by Curtius rearrangment led to 2-chloro-[-2- 14 C] ethyl isocyanate: 9 which finally was condensed with 4-t-butylaniline leading to the title compound (radiochemical purity 99%) in an overall yield of about 10% based on [ 14 C] barium carbonate.