Strategies to Tackle the Waste Water from α-Tocopherol-Derived Surfactant Chemistry

Krell, Christoph; Schreiber, Robert; Hueber, Lukas; Sciascera, Luca; Zheng, Xiaoming; Clarke, Adrian; Haenggi, Ruedi; Parmentier, Michaël; Baguia, Hajar; Rodde, Stephane; Gallou, Fabrice

doi:10.1021/acs.oprd.0c00547

Cited by 52 publications

(76 citation statements)

References 27 publications

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“…Thus, using Sheldon’s associated E Factor as a measure of greenness, and doing the calculation based on the solvents involved (MeOH and water, which make up 88% of the waste typically seen in drug syntheses), the value of 1.07 is indicative of the environmentally responsible nature of this process. Eventually, of course, the water becomes part of the waste stream containing the surfactant; however, recent work by Novartis has outlined the path for dealing with this aspect of the technology …”

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confidence: 99%

“…Eventually, of course, the water becomes part of the waste stream containing the surfactant; however, recent work by Novartis has outlined the path for dealing with this aspect of the technology. 24 As the toolbox of technologies associated with chemistry in water continues to expand, 25 so do the combinations now possible for sequential, one-pot processes that involve a variety of reactions in both the chemo-and, most recently, biocatalysis regimes. 26 The sequence shown in Scheme 3 is illustrative of the dramatic increases of complexity now possible in a singlepot operation, taking advantage of each step being run in the same, aqueous medium.…”

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confidence: 99%

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Bisulfite Addition Compounds as Substrates for Reductive Aminations in Water

Iyer

Thakore

et al. 2021

Org. Lett.

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Highly valued products resulting from reductive aminations utilizing shelf-stable bisulfite addition compounds of aldehydes can be made under aqueous micellar catalysis conditions. Readily available α-picolineborane serves as the stoichiometric hydride source. Recycling of the aqueous reaction medium is easily accomplished, and several applications to targets in the pharmaceutical industry are documented.

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confidence: 99%

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confidence: 99%

Bisulfite Addition Compounds as Substrates for Reductive Aminations in Water

Iyer

Thakore

et al. 2021

Org. Lett.

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“…Furthermore, the methods using Triton X (Table 1, approaches I–III) are hampered by its high toxicity, [34] whereas all methods suffer from the need for large amounts of AAs (≥3 equiv.). Finally, the fact that minimization of the waste was not addressed is a concern as tackling aqueous waste containing organic compounds is challenging [35] . We set out to investigate an aqueous Fmoc/ t‐ Bu SPPS, which by means of using inexpensive standard Fmoc AAs without any processing would be easier to adopt.…”

Section: Methodsmentioning

confidence: 99%

Circular Aqueous Fmoc/t‐Bu Solid‐Phase Peptide Synthesis

Pawlas

Rasmussen

2021

ChemSusChem

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Circular economy and aqueous synthesis are attractive concepts for sustainable chemistry. Here it is reported that the two can be combined in the universal method for peptide chemistry, fluorenylmethoxycarbonyl(Fmoc)/t‐Bu solid‐phase peptide synthesis (SPPS). It was demonstrated that Fmoc/t‐Bu SPPS could be performed under aqueous conditions using standard Fmoc amino acids (AAs) employing TentaGel S as resin and 4 : 1 mixture of water with inexpensive green solvent PolarClean. This resin/solvent combination played a crucial dual role by virtue of improving resin swelling and solubility of starting materials. In a model coupling, TCFH and 2,4,6‐collidine afforded a full conversion at only 1.3 equiv. AA, and these conditions were used in SPPS of Leu enkephaline amide affording the model peptide in 85 % yield and 86 % purity. A method to recycle the waste by filtration through a mixed ion exchange resin was developed, allowing reusing the waste without affecting quality of the peptide. The method herein obviates the use of unconventional or processed AAs in aqueous SPPS while using lower amounts of starting materials. By recycling/reusing SPPS waste the hazardous dipolar aprotic solvents used in SPPS were not only replaced with an aqueous medium, solvent use was also significantly reduced. This opens up a new direction in aqueous peptide chemistry in which efficient use of inexpensive starting materials and waste minimization is coupled with the universal Fmoc/t‐Bu SPPS.

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“…Even the constant concern expressed by representatives from a few companies (as members of the ACS Green Chemistry Institute's (GCI) Pharma Roundtable (PRT)) that the question of waste water produced using chemistry in water has yet to be fully addressed, has been laid to rest by a team from Novartis under the direction of Fabrice Gallou. 52 Moreover, the old argument that it would be 'too costly' has been thoroughly discredited, as from the standpoint of economics, we now know unequivocally (e.g., from the EPA Presidential Green Chemistry Challenge Awards to several companies each year) 53 that going green is always favorable in this regard.…”

Section: Account Synlettmentioning

confidence: 99%

Illuminating a Path4914. Copyright 2016 Wiley for Organic Synthesis Towards Sustainability. No One Said It Would Be Easy…

Lipshutz¹

2021

Synlett

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A personalized account is presented describing some of the stories behind the scenes in efforts to convert organic chemistry into a more sustainable discipline. These are part of a group ‘crusade’ started almost 15 years ago aimed at providing technologies illustrative of how key reactions used today can be ‘faster, better, cheaper’ when run in recyclable water. Hence, the option now exists to do organic synthesis in a far more environmentally responsible fashion. By contrast, most of organic chemistry developed over the past 200 years that relies on organic solvents continues to generate enormous amounts of pollution, while depleting finite petroleum reserves and our supplies of many precious and base metals. Making the switch to water, Nature’s chosen reaction medium, akin to that in which bio-catalysis is typically performed, is inevitable.1 The Story Begins: A Different Type of Prejudice2 Are We up to the Challenge? Too Late Now…3 ‘Impossible’ Reactive Metal Chemistry in Water4 Didn’t I Once Say: ‘It’s All about the Ligand’?5 What Happens When Our Supply of Palladium Runs Out?6 What Are the Implications from These Tales for Today and Tomorrow?7 What Is the ‘Broader Impact’ of This Work?8 The Bottom Line…

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Strategies to Tackle the Waste Water from α-Tocopherol-Derived Surfactant Chemistry

Cited by 52 publications

References 27 publications

Bisulfite Addition Compounds as Substrates for Reductive Aminations in Water

Bisulfite Addition Compounds as Substrates for Reductive Aminations in Water

Circular Aqueous Fmoc/t‐Bu Solid‐Phase Peptide Synthesis

Illuminating a Path4914. Copyright 2016 Wiley for Organic Synthesis Towards Sustainability. No One Said It Would Be Easy…

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