N-[Chloro(dimethylamino)methylene]-N-methylmethanaminium chloride (TMUCl Cl), the reagent of choice for the solid-phase synthesis of anilides |
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| Authors: | Marc Vendrell Ariel Ewenson Fernando Albericio |
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| Affiliation: | a Combinatorial Chemistry Unit, Barcelona Science Park, University of Barcelona, 08028 Barcelona, Spain
b Luxembourg Industries Ltd, 27 Hamered Street, Tel-Aviv 68125, Israel
c Barcelona Biomedical Research Institute, Barcelona Science Park, University of Barcelona, 08028 Barcelona, Spain
d Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain |
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| Abstract: | An effective solid-phase preparation of anilides from supported carboxylic acids is described by their activation as the corresponding acid chlorides with TMUCl Cl. |
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| Keywords: | Ac, acetyl All, allyl Boc, tert-butyloxycarbonyl CDI, 1,1&prime -carbonyldiimidazole Cl-HOBt, 6-chloro-1-hydroxybenzotriazole DCM, dichloromethane DCT, dichlorotriazine DepODhbt, DEPBT, 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4-(3H)-one DIEA, N,N-diisopropylethylamine DMC, 2-chloro-1,3-dimethylimidazolinium chloride DMF, N,N-dimethylformamide Fmoc, 9-fluorenylmethoxycarbonyl HATU, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5-b]pyridinium hexafluorophosphate 3-oxide HCTU, 1-[bis(dimethylamino)methylene]-6-chloro-1H-benzotriazolium hexafluorophosphate 3-oxide HBTU, 1-[bis(dimethylamino)methylene]-1H-benzotriazolium hexafluorophosphate 3-oxide HDTU, O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate HOAt, 1-hydroxy-7-azabenzotriazole(3-hydroxy-3H-1,2,3-triazolo-[4,5-b]pyridine) HOBt, 1-hydroxybenzotriazole HOOBt, HODHbt, 1-oxo-2-hydroxydihydrobenzotriazine HPLC, high performance liquid chromatography NMM, N-methylmorpholine MS, mass spectroscopy NP, normal phase PPHT, 2-[N-phenylethyl-N-propyl]amino-5-hydroxytetralin Ph, phenyl PS, polystyrene PyAOP, (7-azabenzotriazol-1-yloxy)-tris(pyrrolidino)phosphonium hexafluorophosphate PyBOP, benzotriazol-1-yl-N-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate PyClock, 6-chloro-benzotriazol-1-yl-N-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate Rink resin, peptide amide resin SPOS, solid-phase organic synthesis SPPS, solid-phase peptide synthesis t-Bu, tert-butyl TCT, 2,4,6-trichloro[1,3,5]-triazine (cyanuric chloride) TFA, trifluoroacetic acid TFFH, tetramethylfluoroformamidinium hexafluorophosphate TMUCl Cl, N-[chloro(dimethylamino)methylene]-N-methylmethanaminium chloride. Abbreviations used for amino acids follow the IUPAC-IUB Commission of Biochemical Nomenclature in Jones, J. H. J. Pept. Sci. boldFont" >2003, 9, 1-8 |
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