Evaluation of alternative solvents in common amide coupling reactions: replacement of dichloromethane and N,N-dimethylformamide

Macmillan, Donna S.; Murray, Jane; Sneddon, Helen F.; Jamieson, Craig; Watson, Allan J. B.

doi:10.1039/c2gc36900a

Cited by 123 publications

(102 citation statements)

References 50 publications

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“…Reaction specific solvent selection guides are now available [87][88][89], which rank a set of solvents according to the observed performance (not greenness). The requirement of the solvent in chromatography as the mobile phase is so obvious in its importance that solvent guides for this application predate all other tools [90,91], and has now been revived as a research topic [92,93].…”

Section: Discussionmentioning

confidence: 99%

Tools and techniques for solvent selection: green solvent selection guides

Byrne

Jin

Paggiola

et al. 2016

Sustain Chem Process

1,004

737

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Driven by legislation and evolving attitudes towards environmental issues, establishing green solvents for extractions, separations, formulations and reaction chemistry has become an increasingly important area of research. Several general purpose solvent selection guides have now been published with the aim to reduce use of the most hazardous solvents. This review serves the purpose of explaining the role of these guides, highlighting their similarities and differences. How they can be used most effectively to enhance the greenness of chemical processes, particularly in laboratory organic synthesis and the pharmaceutical industry, is addressed in detail.

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Section: Discussionmentioning

confidence: 99%

Tools and techniques for solvent selection: green solvent selection guides

Byrne

Jin

Paggiola

et al. 2016

Sustain Chem Process

1,004

737

View full text Add to dashboard Cite

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“…When the aminophosphonate 7a was reacted with the acid 12 in the presence of benzotriazol-1-yloxytris (dimethylamino)phosphonium hexafluorophosphate (BOP) [27], (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) [28], N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (HATU) [29], and 1-[(1-(cyano-2-ethoxy-2-oxoethylideneaminooxy)-dimethylamino-morpholinomethylene)]methanaminium hexafluorophosphate (COMU) [29] with triethylamine or diethylisopropylamine as additives, the expected amide 20a could not be isolated from the complex reaction mixtures.…”

Section: Methodsmentioning

confidence: 99%

Acyclic nucleoside phosphonates containing the amide bond

et al. 2016

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To study the influence of a linker rigidity and donor–acceptor properties, the P–CH2–O–CHR– fragment in acyclic nucleoside phosphonates (e.g., acyclovir, tenofovir) was replaced by the P–CH2–HN–C(O)– residue. The respective phosphonates were synthesized in good yields by coupling the straight chain of ω-aminophosphonates and nucleobase-derived acetic acids with EDC. Based on the 1H and 13C NMR data, the unrestricted rotation within the methylene and 1,2-ethylidene linkers in phosphonates from series a and b was confirmed. For phosphonates containing 1,3-propylidene (series c) fragments, antiperiplanar disposition of the bulky O,O-diethylphosphonate and substituted amidomethyl groups was established. The synthesized ANPs P–X–HNC(O)–CH2B (X = CH2, CH2CH2, CH2CH2CH2, CH2OCH2CH2) appeared inactive in antiviral assays against a wide variety of DNA and RNA viruses at concentrations up to 100 μM while marginal antiproliferative activity (L1210 cells, IC50 = 89 ± 16 μM and HeLa cells, IC50 = 194 ± 19 μM) was noticed for the analog derived from (5-fluorouracyl-1-yl)acetic acid and O,O-diethyl (2-aminoethoxy)methylphosphonate.Graphical abstract

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“…2-MeTHF has been used in biocatalysis (85,86), organocatalysis (87), and organometallic transformations (88), and biomass processing (84). It has also been identified as a suitable replacement for dichloromethane (89).…”

Section: -Methyltetrahydrofuranmentioning

confidence: 99%