Preparation of N-Substituted N-Arylsulfonylglycines and Their Use in Peptoid Synthesis

Abstract

To increase the chemical diversity accessible with peptoids and peptide-peptoid hybrids, N-alkylated arylsulfonamides were used to prepare side chain protected N-substituted glycines compatible with solid-phase synthesis. The described procedures give access to peptoid monomers bearing a wide variety of functional groups from commercially available amines in four straightforward steps. The prepared N-substituted N-arylsulfonylglycines were used as monomers in solid-phase synthesis to introduce relevant functionalized side chains into peptoid oligomers and peptide-peptoid hybrids.

A Novel and Practical Synthesis of Mavorixafor

“…7 Also, monoprotected 1,4-diaminobutane 10a was prepared in 94% yield by the reaction of 1,4-diaminobutane (10c) with 5 equiv of Boc 2 O in EtOH. 8 In the beginning, the substitution of compound 9 with 10a was designed to form compound 11a, but the experiments proved that it was difficult to get pure 11a in high yield from the reaction. Although many conditions were evaluated, including the base (K 2 CO 3 , Et 3 N, or N,N-diisopropylethylamine), the solvent (CH 3 CN or DMF), and the temperature, the best result was a low yield of only 27% (after purification by column chromatography), which was obtained by the reaction of 9 with 10a (3 equiv) and K 2 CO 3 (1 equiv) in DMF at 48−51 °C.…”

“…As shown in Scheme , 8-chloro-5,6,7,8-tetrahydroquinoline ( 9 ) was prepared in 98% yield by the reaction of compound 2 with 0.9 equiv of trichloroisocyanuric acid in CH 2 Cl 2 . Also, monoprotected 1,4-diaminobutane 10a was prepared in 94% yield by the reaction of 1,4-diaminobutane ( 10c ) with 5 equiv of Boc 2 O in EtOH …”

Convenient two-step synthesis of highly functionalized benzo-fused 1,4-diazepin-3-ones and 1,5-diazocin-4-ones by sequential Ugi and intramolecular S N Ar reactions

“…tert-Butyl (4-aminobutyl)carbamate and 4-tertbutoxybenzylamine building blocks were prepared as previously described. [69][70][71] All other reagents and solvents were purchased from Sigma-Aldrich (St. Louis, MO, USA). Microwave experiments were conducted on a Biotage Initiator microwave instrument (Charlotte, NC, USA) with 0.5-2 mL sealed microwave vials.…”

General Method for Selective Mono-Boc Protection of Diamines and Thereof

“…The addition was carried out at -20 0 C. Using the same work-up procedure as above, the final product tert-Butyl (1R,2R)-2-aminocyclohexylcarbomate (1a) was obtained in 1.24g, 41%. (19), 114 (35), 57 (100). Spectroscopic data were in good agreement with those reported in the literature [19,20].…”

“…(19), 114 (35), 57 (100). Spectroscopic data were in good agreement with those reported in the literature [19,20].…”