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The presence of the morpholino group in conjunction with an oxime derivative\u2014especially ethyl 2\u2010cyano\u20102\u2010(hydroxyimino)acetate (Oxyma)\u2014had a marked influence on the solubilities, stabilities, and reactivities of the reagents. Finally, the new uronium salt derived from Oxyma (COMU) performed extremely well in the presence of only 1\u2005equiv of base, thereby confirming the effect of the hydrogen bond acceptor in the reaction. COMU also showed a less hazardous safety profile than the benzotriazole\u2010based HDMA and HDMB, which exhibited unpredictable autocatalytic decompositions. Furthermore, the Oxyma moiety contained in COMU suggests a lower risk of explosion than in the case of the benzotriazole derivatives.<\/jats:p>","DOI":"10.1002\/chem.200900615","type":"journal-article","created":{"date-parts":[[2009,7,20]],"date-time":"2009-07-20T08:52:25Z","timestamp":1248079945000},"page":"9404-9416","source":"Crossref","is-referenced-by-count":301,"title":["COMU: A Safer and More Effective Replacement for Benzotriazole\u2010Based Uronium Coupling Reagents"],"prefix":"10.1002","volume":"15","author":[{"given":"Ayman","family":"El\u2010Faham","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ramon Subir\u00f3s","family":"Funosas","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rafel","family":"Prohens","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fernando","family":"Albericio","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,9,14]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"Abbreviations not defined in text: Aib \u03b1\u2010aminoisobutyric acid; DIEA N N\u2010diisopropylethylamine; DMF N N\u2010dimethylformamide; HOBt 1\u2010hydroxybenzotriazole; HOAt 7\u2010aza\u20101\u2010hydroxybenzotriazole; N\u2010HATU N\u2010[(dimethylamino)\u20101H\u20101 2 3\u2010triazolo[4 5\u2010b]pyridin\u20101\u2010yl\u2010methylene)\u2010N\u2010methylmethanaminium hexafluorophosphate N\u2010oxide; N\u2010HBTU N\u2010[(1H\u2010benzotriazol\u20101\u2010yl)\u2010(dimethylamino)methylene]N\u2010methylmethanaminium hexafluorophosphate N\u2010oxide; DMCH 4\u2010((dimethyamino)chloromethylene)morpholin\u20104\u2010Iminium hexaflurophosphate HDMA 1\u2010((dimethylimino)morpholino>methyl)3\u2010H\u2010[1 2 3]triazolo[4 5\u2010b]pyridine\u20101\u20133\u2010olate hexafluorophosphate; HDMB 1\u2010((dimethylimino)morpholino>methyl)3\u2010H\u2010benzo[1 2 3]triazolo\u20101\u2010ium\u20103\u2010olate hexafluorophosphate; 6\u2010HDMCB 1\u2010((dimethylimino)morpholino>methyl)3\u2010H\u20106\u2010chlorobenzo[1 2 3] triazolo\u20101\u2010ium\u20103\u2010olate hexafluorophosphate; DMU N N\u2010dimethylmorpholine\u20104\u2010carboxamide; DmPyU N N\u2010Dimethylpiperidine\u20101\u2010carboxamide; MPyU Morpholino(pyrrolidin\u20101\u2010yl)methanone;N\u2010DmPyCH (Chloro(pyrrolidin\u20101\u2010yl)methylene)\u2010N\u2010methylmethanaminium hexafluorophosphate; MPyCH 1\u2010(chloro(morpholino)methylene)pyrrolidinium Hexafluorophosphate; HOTU O\u2010[Cyano(ethoxycarbonyl)methylidene)amino]\u20101 1 3 3\u2010tetramethyluronium Hexafluorophosphate; HdmPyOC 1\u2010[(1\u2010(Cyano\u20102\u2010ethoxy\u20102\u2010oxoethylideneaminooxy)\u2010dimethylamino\u2010pyrrolodinomethylene)] methanaminium Hexafluorophosphate; COMU 1\u2010[(1\u2010(Cyano\u20102\u2010ethoxy\u20102\u2010oxoethylideneaminooxy)\u2010dimethylamino\u2010morpholinomethylene)] methanaminium Hexafluorophosphate; HMPyOC 1\u2010((1\u2010cyano\u20102\u2010ethoxy\u20102\u2010oxoethylideneaminooxy)(morpholino)methylene) pyrrolidinium Hexafluorophosphate; HTODC O\u2010[(Dicyanomethylidene)amino]\u20101 1 3 3\u2010tetramethyluronium Hexafluorophosphate; HDmPyODC 1\u2010[(1\u2010(dicyanomethylideneaminoxy)\u2010dimethylamino\u2010pyrrolodinomethylene)] methanaminium Hexafluorophosphate; HDMODC 1\u2010[(1\u2010(dicyanomethyleneaminooxy)\u2010dimethylamino\u2010morpholinomethylene)] methanaminium Hexafluorophosphate HMPyODC 1\u2010((dicyanomethyleneaminooxy)morpholinomethylene)pyrrolidinium Hexafluorophosphoate; HTODeC O\u2010[(diethoxycarbonylmethylidene)amino]\u20101 1 3 3\u2010tetramethyluronium Hexafluorophosphate; HDMODeC 1\u2010[(1 3\u2010diethyoxy\u20101 3\u2010dioxopropan\u20102\u2010ylideneaminooxy)\u2010dimethylamino\u2010morpholinomethylene)] methanaminium Hexafluorophosphate; HTOPC N\u2010[(cyano(pyridine\u20102\u2010yl)methyleneaminooxy)(dimethylamino)methylene)\u2010N\u2010Methylmethanaminium Hexafluorophosphate; HDMOPC N\u2010[(cyano(pyridine\u20102\u2010yl)methyleneaminooxy)(dimethylamino)methylene)\u2010N\u2010morpholinomethanaminium Hexafluorophosphate; HMPyA 1\u2010(morpholino(pyrrolidinium\u20101\u2010ylidene)methyl)\u20101H\u2010[1 2 3]triazolo[4 5\u2010I]pyridine 3\u2010oxide Hexafluorophospahte; HMPyB 1\u2010(morpholino(pyrrolidinium\u20101\u2010ylidene)methyl)\u20101H\u2010benzo[d][1 2 3]triazole 3\u2010oxide Hexafluorophosphate; HMPyC 5\u2010chloro\u20101\u2010(morpholino(pyrrolidinium\u20101\u2010ylidene)methyl)\u20101H\u2010benzo[d][1 2 3]triazole 3\u2010oxide hexafluorophosphate; Amino acids and peptides are abbreviated and designated following the rules of the IUPAC\u2010IUB Commission of Biochemical Nomenclature [J. 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