Synthesis of a Sulfahydantoin Library

Abstract

A five-step solid-phase synthesis of sulfahydantoins from alpha-amino acids and aldehydes was developed. The synthetic method allows the use of hindered amino acids, including Val, Phg, and Aib, and use of aromatic aldehydes substituted with electron-withdrawing and -donating groups. Some limitations were encountered with amino acids with reactive side chains. A small but diverse library of compounds was produced for biological testing.

Further applications of classical amide coupling reagents: Microwave‐assisted esterification on solid phase

“…Several strategies have been conducted for the addition of ester linkage (s) to solid supports. One of the most common strategies to activate carboxylic acid is through a symmetrical anhydride, prepared with carbodiimide reagents and catalyzed by dimethylaminopyridine (DMAP) . This method works well for regular amino acids, but is not the most appropriate when attaching racemization‐prone amino acid derivatives .…”

“…One of the most common strategies to activate carboxylic acid is through a symmetrical anhydride, prepared with carbodiimide reagents and catalyzed by dimethylaminopyridine (DMAP). [16][17][18][19][20] This method works well for regular amino acids, but is not the most appropriate when attaching racemization-prone amino acid derivatives. 21,22 Under more challenging conditions, 1-(mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT) is the reagent of choice to reduce enantiomerization.…”

Solid-Phase Synthesis of Sulfamate Peptidomimetics

“…The resin was washed with DCM (5 × 1 min) and then was treated with Pd(PPh 3 ) 4 (0.1 equiv) Figure 1. Building blocks (4)(5)(6)(7)(8)(9)(10)(11) used in this study and sulfamated peptidomimetics (12)(13)(14)(15)(16)(17) obtained. in the presence of PhSiH 3 (24 equiv) in DCM under Ar (2 treatments of 20 min).…”

Solid-Phase Synthesis of Azasulfurylphenylalanine4-GHRP-6

“…In solution, activation of valine iso-propylamide with p-nitrophenyl chlorosulfate gave the desired sulfamidate in only 15% yield, presumably because intramolecular cyclization occurred on the C-terminal amide nitrogen to form a sulfahydantoin analog (not isolated) [13]. In conclusion, a solid-phase method was developed for the synthesis of [AsF 4 ]-GHRP-6 (9) featuring the solution-phase synthesis of AsF tripeptide 5 and its application on Rink amide resin.…”