Generating Monofluoro‐Substituted Amines and Amino Acids by the Interaction of Inexpensive KF and Sulfamidates

Abstract

The regioselective ring‐opening of 1,2‐ and 1,3‐sulfamidates with fluorine anion is reported. Direct construction of monofluoro‐substituted amines and amino acid derivatives using inexpensive and easily available potassium fluoride (KF). The monofluorination process only needs 35 minutes under heating, which will be an attractive route for the synthesis of the PET fluorine‐18 radiotracer. The application of the product can be extended to the construction of fluorinated polypeptides after simple deprotection treatment.

Amphiphilic Polyfluorinated Amino Ethers from Cyclic Sulfamidates

“…The ring opening of versatile cyclic sulfamidates by means of fluorinated nucleophiles was reported in the literature that include formation of C–F, ,− C–R F , and C–SCF 3 bonds, but the construction of C–OR F is still a rare disconnection . We have filled this gap by investigating the regioselective ring opening of 1,2- and 1,3-cyclic sulfamidates with diverse polyfluorinated alkoxides.…”

Synthesis and Biological Evaluation of Fluorine-18 and Deuterium Labeled l-Fluoroalanines as Positron Emission Tomography Imaging Agents for Cancer Detection

“…After three sulfamidate precursors were obtained, the synthesis of the nonradioactive reference compounds was performed through fluorination followed by deprotection (Scheme ). Inspired by previously reported nucleophilic displacement reactions with sulfamidates, , fluorinated intermediate 10 was prepared in an 80% yield prepared by nucleophilic monofluoroination of l -sulfamidate 3 with KF and 18-crown-6 in tert -butanol/MeCN followed by the removal of SO 3 – group in 20% H 2 SO 4 /DCM. Once the key intermediate 10 was obtained, optically pure nonradioactive l -3-fluoroalanine 12 was acquired under a mild acidic deprotection condition.…”