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4/13/2015 GEN | Magazine Articles: Green Chemistry Initiatives Take Shape
http://www.genengnews.com/genarticles/greenchemistryinitiativestakeshape/3906/ 1/4
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Gail Dutton
Medicinal Chemistry
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Many innovative companies are embracing green chemistry, citing environmental sustainability,
increased efficiency, and lowered costs, as they develop the tools and measurements that inform the
choices of solvents and reagents throughout a compound’s development and manufacturing,
according to speakers at the American Chemical Society’s (ACS) recent “Green Chemistry and
Engineering” conference.
“Green chemistry is gaining prominence, paralleling regulatory and economic movements. There is a
global expectation for sustainable resource use, chemical safety, and transparency as stakeholders
are becoming more precautionary and risk adverse,” Richard Williams, Ph.D., president and founder
of Environmental Science & Green Chemistry Consulting, said.
“Since 2003, 18 U.S. states have collectively passed 71 chemical control laws calling for the use of
green chemistry, phaseout of specific substances, data collection, or the reduced industrial use of
toxic chemicals.
“Green chemistry is just good chemistry,” Dr. Williams said. “As new science develops, it delivers
economic and environmental benefits. For example, Pfizer improved the manufacturing process for
sertraline, the active ingredient in Zoloft®.”
The original threestep sequence was streamlined to one step, producing chirally pure sertraline in
much higher yield and with greater selectively. Raw material usage for three materials declined by
60%, 45%, and 20%, respectively.
Employing ethanol as a solvent eliminated the use, distillation, and recovery of four more hazardous
solvents. The green approach has eliminated nearly 2 million pounds of chemical waste per year,
improved safety and material handling, reduced energy and water use, and doubled overall product
yield, Dr. Williams reported.
One aspect of Amgen’s sustainability initiative focuses on
medicinal chemistry. “Although the scale of reaction is
small, the cumulative footprint is significant,” noted Emily
Peterson, Ph.D., scientist and green chemistry team lead
Nov 1, 2011 (Vol. 31, No. 19)
Green Chemistry Initiatives Take ShapeEmbracing More Environmentally Friendly Practices Also Has EconomicBenefits
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4/13/2015 GEN | Magazine Articles: Green Chemistry Initiatives Take Shape
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Emily Peterson, Ph.D., Amgen scientist and greenchemistry team lead, applies green chemistryprinciples in her lab at Amgen’s Cambridge Researchfacility.
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Merck and Codexis developed a more efficientprocess for the synthesis of sitagliptin, the activepharmaceutical ingredient in Januvia, enabled by atransaminase developed using Codexis’ platformtechnology to customize biocatalysts derived fromliving organisms. Natural transaminases are inactiveon the prositagliptin ketone due to steric constraintsin the active site. In contrast, the custom biocatalystprovided the desired activity and productivity. Theillustrations show the chiral aldimine intermediatebound in the active site of an in silico model of thecatalyst. The large binding pocket is orange; the smallbinding pocket is blue; the catalytic residues and cofactor are green. Top: processes based on candidatenatural enzymes did not yield the desired molecule.Bottom: The Codexis custom biocatalyst developedwith Merck catalyzed a more efficient process.
for Amgen Massachusetts (AMA) medicinal chemistry.
The goal at Amgen, then, is to “equip medicinal chemists
with working knowledge of green chemistry, provide
access to tools to guide green solvent and reagent
selection, and apply restraint rather than constraint,” to
chemists’ choices. Immediate challenges include
reducing chlorinated solvent usage, phasing out toxic and
noneconomical reagents, modifying wasteful ordering
and disposal habits, and encouraging use of green
conditions.
These changes are seeing results. For example, since
November 2010, the use of dichloromethane at the AMA site has declined 40%. “Ten percent was
achieved just by picking up a different squirt bottle when chemists rinsed their tubes,” Dr. Peterson
explained.
Much of the rest was achieved by education and replacing dichloromethane chromatography with
greener solvent systems (like heptanes, ethyl acetate, and ethanol) and by replacing normalphase
chromatography with reversephase mediumpressure liquid chromatography, which allows
purification of highly polar compounds using aqueous media.
“You can load large amounts onto the column, including crude reaction mixtures, and you can reuse
the columns, which gives nice flexibility,” Dr. Peterson added.
At Amgen, “we also crafted our own green chemistry solvent selection guide. We made it into
magnets and put them on all the hoods, so chemists are reminded daily of greener options.”
At Dr. Peterson’s site, the T3P amide coupling reagent has become a popular reagent in medicinal
chemistry, she said. “You can work it up with water, and the product is often pure enough to go to the
next step without contamination with other reagents.”
To reduce waste, Amgen partners with ASDI to store its chemicals. Therefore, research sites can
order just the quantities they need from among Amgen’s own supplies. The company also changed its
chemical disposal policy, retaining chemicals with longterm stability rather than discarding all
chemicals after three years. In shipping 500 compounds to ASDI, “we saved $3,000 on disposal
alone.”
Chemists contemplating green chemistry cite concerns about reoptimization timeframes, costs,
access to established chemicals, or methods and regulatory issues. “The key to adoption is to use
green technologies that are superior to current methods.” Amgen also operates a green chemistry
awards program for labs that make the greatest green chemistry gains. “Cash talks,” she said.
Ingrid Mergelsberg, Ph.D., director of process chemistry
at Merck and immediate past cochair of the ACS Green
Chemistry Institute Pharmaceutical Roundtable (GCIPR),
agreed. “Since 2007, the Roundtable has awarded
$950,000 in research grants based on green principles
and formed academic liaisons with industry.”
Roundtable members lead by example. “Merck has
pioneered advances in areas such as asymmetric and
enzymatic catalysis, highthroughput screening in
catalysis, and supercritical fluid chromatography for chiral
and achiral separations, which avoid the creation of
significant amounts of solvent waste,” Dr. Mergelsberg
said.
To create a green chemistry environment, “it’s essential
to have routine demonstrations of commitment to green
chemistry and engineering from senior management.
We’ve implemented a crossfunctional green chemistry
team with measurable goals and objectives supported by
senior management. Merck has also created a green
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4/13/2015 GEN | Magazine Articles: Green Chemistry Initiatives Take Shape
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chemistry elearning course that will be available in the next few months, and a green chemistry
toolbox.
“Tools are very powerful to facilitate chemists getting greener,” Dr. Mergelsberg continued. Merck’s
own green chemistry toolbox includes a process mass intensity (PMI) and analytical method volume
intensity total solvent consumption calculator, solvent selection guide, pathway to greener solvents,
and a reagent selection guide tool kit for enzymatic and catalytic reactions.
By 2020, the Roundtable plans to have a database of highly efficient transformations, a predictive tool
for greener route design, and standard quantitative key performance indicators and measures of
greenness.”
Merck has developed its own green chemistry electronic notebook templates based on the reagent
selection guide. The Roundtable has initiated discussions with enotebook suppliers.
She also aims to influence the research agenda. “Most chemistry journals haven’t embraced green
chemistry policies and principles yet. In many broadly referenced articles, chloroform, benzene, and
other absolutely nongreen solvents and reagents are still used. Thus, medicinal chemists naturally
start with nongreen reagents because they are following established protocols.”
Dr. Mergelsberg sees progress, however. “Organic Process Research and Development has
accepted some of the Roundtable’s wishes, by not accepting papers with solvents of benzene or of
chloroform.”
The Roundtable is also preparing a reagent selection guide. Its goal is to identify the most
environmentally benign conditions for chemical transformations and analyze reactions for five green
criteria: the environmental degradation of reagent and degradation products, solvent compatibility to
green solvents, availability from natural feedstocks, atom efficiency of transformation, and toxicity and
process safety hazards.
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4/13/2015 GEN | Magazine Articles: Green Chemistry Initiatives Take Shape
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