Efficient synthesis of (2S)-tert-butyl 2-(2-bromopropanamido)-5-oxo-5-(tritylamino)pentanoate as a precursor of PET radiotracer [18F]FPGLN. Issue 12 (18th June 2017)

• Record Type: Journal Article
• Authors: Liu, Shaoyu; Tang, Xiaolan; Nie, Dahong; Jiang, Shende; Tang, Ganghua
• Is Part Of: Synthetic communications. Volume 47:Issue 12(2017)
• Page Start: 1136
• Page End: 1141
• Publication Date: 2017-06-18
• Subjects: Glutamine derivatives -- new precursor -- positron emission tomography -- radiotracer; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2017.1315671
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: This study describes a convenient protocol for the synthesis of (2 S )- tert -butyl 2-(2-bromopropanamido)-5-oxo-5-(tritylamino)pentanoate, which can serve as an appropriate precursor of (2 S )-5-amino-2-(2-[ 18 F]fluoropropanamido)-5-oxopentanoic acid ( N -(2-[ 18 F]fluoropropionyl)-L -glutamine, [ 18 F]FPGLN) for tumor positron emission tomography imaging. Five-step synthesis starting fromL -glutamine provided the desired precursor with high yields. In addition, a simple method for the preparation of [ 18 F]FPGLN from this easily available precursor was developed using a two-step 18 F-labeling strategy. GRAPHICAL ABSTRACT: