a-radiolabeling of sterically congested Amides – UROP Spring Symposium 2022

a-radiolabeling of sterically congested Amides

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Richard Ma

Pronouns: He/Him/His

Research Mentor(s): Peter Scott
Co-Presenter:
Research Mentor School/College/Department: Nuclear Medicine/Radiology / Medicine
Presentation Date: April 20
Presentation Type: Oral5
Session: Session 6 – 4:40pm – 5:30 pm
Room: Breakout room 3
Authors:
Presenter: 2

Abstract

A silver promoted substitution reaction at the alpha position of highly sterically hindered amide has been shown. A study was undertaken to investigate the possibility of using different methods and additives to achieve high radiochemical conversion that does not involve silver. Fluorine-18 was produced in a cyclotron via the 18O, 18F nuclear reaction with a 2 minutes beam at 55uA and trapped on a Waters QMA SepPak Light preconditioned with 0.5M of KOTf. Then the fluorine was eluted with 0.5 ml Cs2CO3 in 0.5 ml H2O and azeotropically dried at 100 with [3,4]-Dibenzo-21-crown-7 in 1ml MeCN. Redissolved in 5ml MeCN. Following reaction in 500 uL solvent for allotted time analyze via rTLC and rHPLC. 14 reactions with 1 equivalence of 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) is prepared. TBD is pre-weighted into a scintillation vial and dissolved in 2.8 ml of MeCN, then added to the reaction vials with Fluorine-18 and extra MeCN where needed. By selecting the optimal reaction conditions, with reaction time of 45 minutes and reaction temperature at 80, we were able to achieve a 39.8 percent radiochemical conversion rate. Further studies need to be conducted to see the effects of change in base equivalency and effects of additional additives (i.e. Iodine via KI, TMAI, etc,…), and to better understand the mechanism of this reaction.

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Engineering, Interdisciplinary, Natural/Life Sciences

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