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Synthesis of a radiolabeled type A cholecystokinin receptor antagonist, ( R )‐N‐pentyl‐N‐(4,5‐di[ 3 H]pentyl) N α ‐(3‐quinolinoyl)glutamic acid amide
Author(s) -
Malone Justin A.,
Reidelberger Roger D.,
Hulce Martin
Publication year - 2000
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(200001)43:1<77::aid-jlcr292>3.0.co;2-v
Subject(s) - chemistry , amide , hydrogenolysis , stereochemistry , dichloromethane , moiety , glutamic acid , dipeptide , antagonist , amino acid , medicinal chemistry , receptor , organic chemistry , catalysis , biochemistry , solvent
A method for the preparation of a radiolabeled CCK A ‐specific antagonist,( R )‐N‐pentyl‐N‐(4,5‐di[ 3 H]pentyl) N α ‐(3‐quinolinoyl)glutamic acid amide, [ 3 H]‐A‐65186, is described. ( R )‐γ‐Benzyl‐N‐BOC‐glutamic acid was coupled with N‐(4‐pentenyl)‐N‐pentylamine using BOPCl and TEA in dichloromethane to provide the corresponding amide. Deprotection of the α‐amino moiety followed by coupling with 3‐quinolinecarboxylic acid in the presence of EDCI, TEA, and HOBt in dichloromethane resulted in ( R )‐N‐(4‐pentenyl)‐N‐pentyl γ‐benzyl‐N α ‐(3‐quinolinoyl)glutamic acid amide. Tritiation with concomitant hydrogenolysis of the benzyl ester proceeds smoothly to provide [ 3 H]‐A‐65186. Copyright © 2000 John Wiley & Sons, Ltd.