Syntheses of carbon‐14 labelled AJ‐9677, a specific β 3 ‐adrenoceptor agonist

Two 14 C‐labelled versions of AJ‐9677, a novel anti‐diabetic drug candidate, have been synthesized. The first, [acetic acid‐2‐ 14 C]AJ‐9677, was synthesized via a four‐step process starting from 2‐chloro‐ N,N ‐diethyl[2‐ 14 C]acetamide ( 3 ), and the second, [hydroxymethine‐ 14 C]AJ‐9677, by a two step process from ( R )‐3‐chloro[7‐ 14 C]styrene oxide ( 8 ). When stored in the solid state both compounds undergo radiolytic decomposition in a similar manner, despite the labelled position being different, to give the dechlorinated derivative ( 12a, 12b ). Purification of the required product was achieved after derivatization to the methyl esters. Copyright © 2004 John Wiley & Sons, Ltd.