Synthesis of N-phthalimido β-aminoethanesulfonyl chlorides: the use of thionyl chloride for a simple and efficient synthesis of new peptidosulfonamide building blocks

A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system

“…After finding the optimal reaction conditions, we studied the methodology with an array of commercially available aromatic and aliphatic carboxylic acids with benzylamine (Table 3, entries [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. In comparison, aromatic carboxylic acids with electron deficient substituents were successfully reacted with benzylamine very rapidly than electron-rich aromatic carboxylic acids (e.g.…”

“…Reasonable yields were obtained when solvents such as THF, CHCl 3 , 1,4-dioxane, acetone, and hexane were used ( Table 5, entries 3-7). Both PPh 3 /NCBT system and solvent play essential role in preparation of product (Table 5, entries [8][9][10][11]. We also tested the influence of various molar ratios of PPh 3 /NCBT/RSO 3 H/R'R"NH on the model reaction, since it was expected, the reaction rate was decreased by decreasing the amount of PPh 3 , NCBT or R'R"NH (Table 5, entries [12][13][14][15].…”

“…8 We were pleased to find the new protocol allows extending the method from aliphatic and aromatic sulfonic acids to the less reactive aromatic sulfonic acids and amines (Table 6).…”

Structure−Affinity Relationships of Glutamine Mimics Incorporated into Phosphopeptides Targeted to the SH2 Domain of Signal Transducer and Activator of Transcription 3

“…The latter was prepared by treating the sodium salt of Fmoc-3-aminopropane sulphonic acid ( 60 ) with SOCl 2 /DMF (cat)37. Peptide 15 was initiated by coupling of Fmoc-4-Abu-OH to hydroxylamine resin using DIPCDI/HOBt, followed by assembly of the rest of the amino acids.…”

Thionyl Chloride - A Versatile Reagent

“…It reacts with most carbonyl or aromatic sulfoacid compounds to give carboxylic acids or aromatic sulfochlorides, respectively. 3,4 (B) A monochloroxime steroid reacts with thionyl chloride in the presence of pyridine traces in benzene via an abnormal Beckmann rearrangement. 5 (C) Chlorination of amino alcohols with thionyl chloride gives chloroethyl amides; if excess thionyl chloride is used, the reaction yields chloroethyl imidoyl chlorides.…”