Cited by 572

The DOI matches its Crossref record; 16 of the 16 references it cites were found in a registry or an index.

Design of Experiments (DoE) and Process Optimization. A Review of Recent Publications

Weissman, Steven A., Anderson, Neal G.·2015·Organic Process Research & Development

Open this paper in CoChat — free account

Abstract

Statistical design of experiments (DoE) is a powerful tool for optimizing processes, and it has been used in many stages of API development. This review summarizes selected publications from Organic Process Research & Development using DoE to show how processes can be optimized efficiently and how DoE findings may be applied to scale-up.

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

Integrity signals

Registry

Crossref · 10.1021/op500169m

Cites

16 of 16 references verified0 citation errors · 0 not checkable

Statistics

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Statistics for Experimenters
Addelman, S. (1979) · Technometrics · doi:10.1080/00401706.1979.10489788 · Cited by 6,750
Homeopathic Ligand-Free Palladium as a Catalyst in the Heck Reaction. A Comparison with a Palladacycle
de Vries, A. H. M., Mulders, J. M. C. A., Mommers, J. H. M., Henderickx, H. J. W., & de Vries, J. G. (2003) · Organic Letters · doi:10.1021/ol035184b · Cited by 551
Design and Optimization in Organic Synthesis
(1992) · Data Handling in Science and Technology · doi:10.1016/s0922-3487(08)x7011-x · Cited by 403
A Reassessment of the Transition-Metal Free Suzuki-Type Coupling Methodology
Arvela, R. K., Leadbeater, N. E., Sangi, M. S., Williams, V. A., Granados, P., & Singer, R. D. (2005) · The Journal of Organic Chemistry · doi:10.1021/jo048531j · Cited by 384
Unification of Reaction Metrics for Green Chemistry: Applications to Reaction Analysis
Andraos, J. (2005) · Organic Process Research & Development · doi:10.1021/op049803n · Cited by 217
Crystallization-Induced Diastereomer Transformations
Brands, K. M. J., & Davies, A. J. (2006) · Chemical Reviews · doi:10.1021/cr0406864 · Cited by 211
A New and Simplified Process for Preparing N -[4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine and a Telescoped Process for the Synthesis of (1 S - cis )-4-(3,4-Dichlorophenol)-1,2,3,4-tetrahydro- N -methyl-1-naphthalenamine Mandelate: Key Intermediates in the Synthesis of Sertraline Hydrochloride
Taber, G. P., Pfisterer, D. M., & Colberg, J. C. (2004) · Organic Process Research & Development · doi:10.1021/op0341465 · Cited by 101
Mechanism and Processing Parameters Affecting the Formation of Methyl Methanesulfonate from Methanol and Methanesulfonic Acid: An Illustrative Example for Sulfonate Ester Impurity Formation
Teasdale, A. J., Eyley, S. C., Delaney, E., Jacq, K., Taylor-Worth, K., Lipczynski, A. M., Reif, V. D., Elder, D. P., Facchine, K. L., Golec, S., et al. (2009) · Organic Process Research & Development · doi:10.1021/op800192a · Cited by 74
A Detailed Study of Sulfonate Ester Formation and Solvolysis Reaction Rates and Application toward Establishing Sulfonate Ester Control in Pharmaceutical Manufacturing Processes
Teasdale, A. J., Delaney, E. J., Eyley, S. C., Jacq, K., Taylor-Worth, K., Lipczynski, A. M., Hoffmann, W., Reif, V. D., Elder, D. P., Facchine, K. L., et al. (2010) · Organic Process Research & Development · doi:10.1021/op900301n · Cited by 70
Seven Important Elements for an Effective Green Chemistry Program: An IQ Consortium Perspective
Leahy, D. K., Tucker, J. L., Mergelsberg, I., Dunn, P. J., Kopach, M. E., & Purohit, V. C. (2013) · Organic Process Research & Development · doi:10.1021/op400192h · Cited by 52
Demonstration on Pilot-Plant Scale of the Utility of 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) as a Catalyst in the Efficient Amidation of an Unactivated Methyl Ester
(2012) · doi:10.1021/op300210j · Cited by 42
Chemical Development on the Chiral Auxiliary (S)-4-(Phenylmethyl)-2-oxazolidinone Utilizing Automated Synthesis and DoE
Vo, L. P., Ciula, J. C., & Gooding, O. W. (2003) · Organic Process Research & Development · doi:10.1021/op034033l · Cited by 36
Development of a Scaleable Process for the Synthesis of a Next-Generation Statin
Hobson, L. A., Akiti, O., Deshmukh, S. S., Harper, S., Katipally, K. R., Lai, C. J., Livingston, R. C., Lo, E. T., Miller, M. M., Ramakrishnan, S., et al. (2010) · Organic Process Research & Development · doi:10.1021/op100010n · Cited by 35
Development and Scale-Up of an Optimized Route to the Peptide Boronic Acid, CEP-18770
Roemmele, R. C., & Christie, M. A. (2013) · Organic Process Research & Development · doi:10.1021/op400010u · Cited by 25
Development of a Practical and Efficient Synthesis of CP-945,598-01, a CB1 Antagonist for the Treatment of Obesity
Ragan, J. A., Bourassa, D. E., Blunt, J., Breen, D., Busch, F. R., Cordi, E. M., Damon, D. B., Đỗ, N., Engtrakul, A., Lynch, D., et al. (2008) · Organic Process Research & Development · doi:10.1021/op800255j · Cited by 16
Development of Synthetic Routes, via a Tropinone Intermediate, to a Long-Acting Muscarinic Antagonist for the Treatment of Respiratory Disease
Bream, R. N., Hayes, D., Hulcoop, D. G., & Whiteman, A. J. (2013) · Organic Process Research & Development · doi:10.1021/op3002933 · Cited by 10

Research works printed but not linked: 85

Laird T., 2002, Org. Process Res. Dev., 6, 337, 10.1021/op0255581 · doi:10.1021/op0255581
Mills J. E., 2003, Chemical Process Research, 87, 10.1021/bk-2004-0870.ch006 · doi:10.1021/bk-2004-0870.ch006
Mullin R., 2013, Chem. Eng. News, 25, 10.1021/cen-09113-bus2 · doi:10.1021/cen-09113-bus2
Ritter S. K., 2002, Chem. Eng. News, 80, 19, 10.1021/cen-v080n047.p019 · doi:10.1021/cen-v080n047.p019
Anderson N. G., 2011, Org. Process Res. Dev., 15, 162, 10.1021/op1002825 · doi:10.1021/op1002825
Looker A. R., 2010, Org. Process Res. Dev., 14, 1032, 10.1021/op900338g · doi:10.1021/op900338g
Lendrem D., 2001, Org. Process Res. Dev., 5, 324, 10.1021/op000025i · doi:10.1021/op000025i
Pilipauskas D. R., 1999, Process Chemistry in the Pharmaceutical Industry
Kuethe J. T., 2009, Org. Process Res. Dev., 13, 471, 10.1021/op8002739 · doi:10.1021/op8002739
Bacchi S., 2010, Org. Process Res. Dev., 14, 332, 10.1021/op900286r · doi:10.1021/op900286r
Reid G. L., Am. Pharm. Rev.
DelMonte A. J., 2011, Org. Process Res. Dev., 15, 64, 10.1021/op100225g · doi:10.1021/op100225g
Mobele B. I., 2012, Org. Process Res. Dev., 16, 1385, 10.1021/op3000916 · doi:10.1021/op3000916
Banks A., 2009, Org. Process Res. Dev., 13, 1130, 10.1021/op9001824 · doi:10.1021/op9001824
Hajmowicz H., 2011, Org. Process Res. Dev., 15, 427, 10.1021/op100315k · doi:10.1021/op100315k
Weiberth F. J., 2010, Org. Process Res. Dev., 14, 623, 10.1021/op100053k · doi:10.1021/op100053k
Manoel E. A., 2012, Org. Process Res. Dev., 16, 1378, 10.1021/op300063f · doi:10.1021/op300063f
Guercio G., 2009, Org. Process Res. Dev., 13, 1100, 10.1021/op9002032 · doi:10.1021/op9002032
Cimarosti Z., 2010, Org. Process Res. Dev., 14, 805, 10.1021/op1000622 · doi:10.1021/op1000622
Guercio G., 2010, Org. Process Res. Dev., 14, 840, 10.1021/op100097c · doi:10.1021/op100097c
Argentine M. D., 2009, Org. Process Res. Dev., 13, 131, 10.1021/op8002486 · doi:10.1021/op8002486
Goodman S. N., 2011, Org. Process Res. Dev., 15, 123, 10.1021/op100266s · doi:10.1021/op100266s
Barton B., 2005, Org. Process Res. Dev., 9, 70, 10.1021/op049844j · doi:10.1021/op049844j
Hida T., 2010, Org. Process Res. Dev., 14, 289, 10.1021/op900265h · doi:10.1021/op900265h
Hida T., 2009, Tetrahedron, 65, 270, 10.1016/j.tet.2008.10.056 · doi:10.1016/j.tet.2008.10.056
Quittmann W., 2004, Org. Process Res. Dev., 8, 1036, 10.1021/op040014f · doi:10.1021/op040014f
Rossi F., 2008, Org. Process Res. Dev., 12, 322, 10.1021/op7001112 · doi:10.1021/op7001112
Radhamani K. N., 1993, J. Fluorine Chem., 95, 10.1016/S0022-1139(00)80065-2 · doi:10.1016/s0022-1139(00)80065-2
Hanselmann R., 2009, Org. Process Res. Dev., 13, 54, 10.1021/op800238q · doi:10.1021/op800238q
Moseley J. D., 2003, Org. Process Res. Dev., 7, 58, 10.1021/op020065h · doi:10.1021/op020065h
Bayat Y., 2011, Org. Process Res. Dev., 15, 810, 10.1021/op200056j · doi:10.1021/op200056j
Bayat Y., 2012, Org. Process Res. Dev., 16, 1733, 10.1021/op300162d · doi:10.1021/op300162d
Guercio G., 2008, Org. Process Res. Dev., 12, 1188, 10.1021/op800146d · doi:10.1021/op800146d
Anderson N. G., 2005, Org. Process Res. Dev., 9, 800, 10.1021/op050119y · doi:10.1021/op050119y
Bravo F., 2010, Org. Process Res. Dev., 14, 832, 10.1021/op1000836 · doi:10.1021/op1000836
Alorati A. D., 2012, Org. Process Res. Dev., 16, 1947, 10.1021/op300303p · doi:10.1021/op300303p
Chaplin D., 2003, Org. Process Res. Dev., 7, 89, 10.1021/op025585r · doi:10.1021/op025585r
Appell R. B., 2013, Org. Process Res. Dev., 17, 69, 10.1021/op3002855 · doi:10.1021/op3002855
Dirat O., 2011, Org. Process Res. Dev., 15, 1010, 10.1021/op200107g · doi:10.1021/op200107g
Guercio G., 2009, Org. Process Res. Dev., 13, 489, 10.1021/op8002823 · doi:10.1021/op8002823
Alimardanov A. R., 2004, Org. Process Res. Dev., 8, 834, 10.1021/op040204q · doi:10.1021/op040204q
Nadkarni D. V., 2008, Org. Process Res. Dev., 12, 1142, 10.1021/op800105j · doi:10.1021/op800105j
Gooding O. W., 2010, Org. Process Res. Dev., 14, 119, 10.1021/op9002246 · doi:10.1021/op9002246
Zhang P., 2005, Org. Process Res. Dev., 9, 583, 10.1021/op050051m · doi:10.1021/op050051m
Massari L., 2010, Org. Process Res. Dev., 14, 1364, 10.1021/op100176u · doi:10.1021/op100176u
Humphrey G. R., 2011, Org. Process Res. Dev., 15, 73, 10.1021/op100257r · doi:10.1021/op100257r
Hopes P. A., 2006, Org. Process Res. Dev., 10, 808, 10.1021/op060057r · doi:10.1021/op060057r
Brenek S. J., 2012, Org. Process Res. Dev., 16, 1348, 10.1021/op300131e · doi:10.1021/op300131e
Barrios Sosa A. C., 2011, Org. Process Res. Dev., 15, 449, 10.1021/op100335q · doi:10.1021/op100335q
Gopalsamy A., 2007, Org. Process Res. Dev., 11, 450, 10.1021/op700009t · doi:10.1021/op700009t
Corona J. A., 2010, Org. Process Res. Dev., 14, 712, 10.1021/op100026u · doi:10.1021/op100026u
Aggarwal V. K., 2006, Org. Process Res. Dev., 10, 64, 10.1021/op058013q · doi:10.1021/op058013q
Cai C., 2007, Org. Process Res. Dev., 11, 328, 10.1021/op060215e · doi:10.1021/op060215e
Nishimura K., 2012, Org. Process Res. Dev., 16, 225, 10.1021/op200312m · doi:10.1021/op200312m
Van Arnum S. D., 2004, Org. Process Res. Dev., 8, 769, 10.1021/op049908q · doi:10.1021/op049908q
Vedantham R., 2013, Org. Process Res. Dev., 17, 798, 10.1021/op3002596 · doi:10.1021/op3002596
For a review of escitalopram syntheses, see:Harrington, P. J.Pharmaceutical Process Chemistry for Synthesis; Rethinking the Routes to Scale-Up;Wiley-VCH; 2011; pp30–91.
Alam M., 2012, Org. Process Res. Dev., 16, 435, 10.1021/op200329x · doi:10.1021/op200329x
Lawrence R. M., 2008, Org. Process Res. Dev., 12, 294, 10.1021/op7002776 · doi:10.1021/op7002776
Raw S. A., 2011, Org. Process Res. Dev., 15, 688, 10.1021/op200079g · doi:10.1021/op200079g
Bullock K. M., 2009, Org. Process Res. Dev., 13, 303, 10.1021/op800211c · doi:10.1021/op800211c
Synoradzki L., 2005, Org. Process Res. Dev., 9, 18, 10.1021/op030029y · doi:10.1021/op030029y
Kirschning A., 2013, Beilstein J. Org. Chem., 9, 1696, 10.3762/bjoc.9.193 · doi:10.3762/bjoc.9.193
Anderson N. G., 2012, Org. Process Res. Dev., 16, 852, 10.1021/op200347k · doi:10.1021/op200347k
Nieuwland P. J., 2011, Org. Process Res. Dev., 15, 783, 10.1021/op100338z · doi:10.1021/op100338z
Koch K., 2009, Org. Process Res. Dev., 13, 1003, 10.1021/op900139u · doi:10.1021/op900139u
Anderson B. G., 2012, Org. Process Res. Dev., 16, 967, 10.1021/op200346g · doi:10.1021/op200346g
Tinder R., 2009, Org. Process Res. Dev., 13, 1401, 10.1021/op900078t · doi:10.1021/op900078t
Vörös A., 2012, Org. Process Res. Dev., 16, 1717, 10.1021/op300113w · doi:10.1021/op300113w
10.1021/op400179f · doi:10.1021/op400179f
Junior I. I., 2012, Org. Process Res. Dev., 16, 1098, 10.1021/op200132y · doi:10.1021/op200132y
Sleveland D., 2012, Org. Process Res. Dev., 16, 1121, 10.1021/op3000493 · doi:10.1021/op3000493
Sjövall S., 2004, Org. Process Res. Dev., 8, 802, 10.1021/op049904l · doi:10.1021/op049904l
Cimarosti Z., 2010, Org. Process Res. Dev., 14, 1337, 10.1021/op100150b · doi:10.1021/op100150b
Pu Y.-M., 2005, Org. Process Res. Dev., 9, 45, 10.1021/op049809c · doi:10.1021/op049809c
Cimarosti Z., 2010, Org. Process Res. Dev., 14, 993, 10.1021/op900242x · doi:10.1021/op900242x
Bravo F., 2010, Org. Process Res. Dev., 14, 1162, 10.1021/op100121s · doi:10.1021/op100121s
Létinois U., 2013, Org. Process Res. Dev., 17, 427, 10.1021/op300190s · doi:10.1021/op300190s
Andemichael Y., 2009, Org. Process Res. Dev., 13, 729, 10.1021/op900104g · doi:10.1021/op900104g
de Koning P. D., 2011, Org. Process Res. Dev., 15, 1081, 10.1021/op200145j · doi:10.1021/op200145j
Delhaye L., 2007, Org. Process Res. Dev., 11, 1104, 10.1021/op600275g · doi:10.1021/op600275g
Chen J. J., 2003, Org. Process Res. Dev., 7, 313, 10.1021/op034018g · doi:10.1021/op034018g
Grabarnick M., 2003, Org. Process Res. Dev., 7, 237, 10.1021/op020075i · doi:10.1021/op020075i
Alozie D.-M., 2011, Org. Process Res. Dev., 15, 1412, 10.1021/op200093b · doi:10.1021/op200093b
Musters J., 2013, Org. Process Res. Dev., 17, 87, 10.1021/op300292a · doi:10.1021/op300292a

Bayesian reaction optimization as a tool for chemical synthesis
Shields, B. J., Stevens, J., Li, J., Parasram, M., Damani, F., Alvarado, J. I. M., Janey, J. M., Adams, R. P., & Doyle, A. G. (2021) · Nature · doi:10.1038/s41586-021-03213-y · Cited by 1,063
Big-Data Science in Porous Materials: Materials Genomics and Machine Learning
Jablonka, K. M., Ongari, D., Moosavi, S. M., & Smit, B. (2020) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00004 · Cited by 599
A field guide to flow chemistry for synthetic organic chemists
Capaldo, L., Wen, Z., & Noël, T. (2023) · Chemical Science · doi:10.1039/d3sc00992k · Cited by 402
The Development of Multidimensional Analysis Tools for Asymmetric Catalysis and Beyond
Sigman, M. S., Harper, K. C., Bess, E. N., & Milo, A. (2016) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00194 · Cited by 357
How To Optimize Materials and Devices via Design of Experiments and Machine Learning: Demonstration Using Organic Photovoltaics
Cao, B., Adutwum, L. A., Oliynyk, A. O., Luber, E. J., Olsen, B. C., Mar, A., & Buriak, J. M. (2018) · ACS Nano · doi:10.1021/acsnano.8b04726 · Cited by 316

See all 572

Authors: Weissman, S. A., & Anderson, N. G.
Venue: Organic Process Research & Development
Publisher: American Chemical Society (ACS)
Published: 2014-08-29
Volume: 19
Issue: 11
Pages: 1605-1633
ISSN: 1083-6160 (ISSN-L)
1520-586X
DOI: 10.1021/op500169m
OpenAlex: W2045293316
Cited by: 572
References: 16
FWCI: 12.73
Type: journal article
Language: en
Open access: closed

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Data sources

Bibliographic data: Semantic Scholar, OpenAlex, Crossref.

Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.

Design of Experiments (DoE) and Process Optimization. A Review of Recent Publications

Abstract

Overview

Integrity signals

Verification

Claims the paper makes

Self-check

Citations

Cites

Cited by

Metadata

Record

About these checks

Data sources