1. Li Zhang January 5, 2017
37 Outlook Rd.
New Milford, CT 06776
Phone: (860) 354-2841
Email: lizhang73@hotmail.com
PSB3721
Boehringer Ingelheim Pharm. Inc.
900 Ridgebury Rd.
Ridgefield, CT 06877
Phone: (203) 798-5724
Email: li.zhang@boehringer-ingelheim.com
HIGHLIGHTS
• Key contribution in Jardiance® (Empagliflozin) development.
• Highly experienced in synthetic route mapping, process researching, developing and technology
transfer.
• Problem solving experiences from milligram scale to 100 kilogram scale.
• Familiar with both GMP and non-GMP operations.
• Excellent track record for Kilo-lab and pilot plant campaign organizing and executing.
• Familiar with all modern instrumentations such as NMR, HPLC, LC-MS, GC, GC-MS, IR and
automation.
• Excellent communication skills.
• Actively interact with many disciplines.
• Favorite team player in all projects.
EDUCATION BACKGROUND
August 1997 – Dec. 1999: Chemistry Department of Iowa State University. Received M.S. in organic
chemistry under Prof. Richard C. Larock
Sept. 1994 - June 1997: Chemistry Department of Nanjing University. Received M.S. in Polymer
Chemistry under Prof. Jian Shen
Sept. 1990 - July 1994: Chemistry Department of Nanjing University. Received B.S. in Chemistry under
Prof. Jian Shen
WORKING EXPERIENCE
From July 2010-present: Senior scientist, Chemical Development, Boehringer-Ingelheim Pharmaceuticals,
Inc.
• Served as representative of Chemical Development in charge of BI1021958, BI1060469,
BI685509 and BI685981 projects.
• Saved company millions of dollars by drastically reducing production cost via innovation
• Solved urgent problems for other colleagues’ projects in short period of time and delivered results
beyond expectation.
From Jan. 2006-July 2010: Senior research associate, Chemical Development, Boehringer-Ingelheim
Pharmaceuticals, Inc.
• Actively involved in the development of BI10773, BI54499, BI671800, BI224436, BI666877,
BI230588, BI1021958 and BI226608.
• Developed the process for Jardiance® (Empagliflozin).
2. • Closely worked with colleagues in other countries to ensure the successful technology transfer,
NDA filing and launch of Jardiance® (Empagliflozin).
From July 2003-Dec. 2005: Research associate, Chemical Development, Boehringer-Ingelheim
Pharmaceuticals, Inc.
• Actively involved in the development of BIRT1696, BIRT2584, BI00607812, BI00212350,
BI00212540 and BI10773.
• Actively worked with multi-discipline team from med-chem support to clinical trial.
• Excellent track record in fast problem solving in process research, Kilo-lab and pilot plant.
From Dec. 1999-July 2003: Senior research assistant, Chemical Development, Boehringer-Ingelheim
Pharmaceuticals, Inc.
• Actively involved in the development of BIRT1696, BIRT2584, BILN1941 and BILN2061.
• Excellent track record in fast problem solving in process research, Kilo-lab and pilot plant.
PUBLICATIONS
1. Structure Elucidation of Poly-Faldaprevir: Polymer Backbone Solved Using Solid-State and
Solution Nuclear Magnetic Resonance Spectroscopy, Gonnella, N. C.; Busacca, C. A.; Zhang, L.;
Saha, A.; Wu, J-P.; Li, G.; Davis, M.; Offerdahl, T.; Jones, P-J.; Herfurth, L. Journal of
Pharmaceutical Sciences, 2016, 105, 1881.
2. Efficient Asymmetric Synthesis of Structurally Diverse P-Stereogenic Phosphinamides for
Catalyst Design, Han, Z. S.; Zhang, L.; Xu, Y.; Sieber, J. D.; Marsini, M. A.; Li, Z.; Reeves, J. T.;
Fandrick, K. R.; Patel, N. D.; Desrosiers, J-N; Qu, B.; Chen, A.; Rudzinski, D. M.; Samankumara,
L. P.; Ma, S.; Grinberg, N.; Roschangar, F.; Yee, N. K.; Wang, G.; Song, J. J.; Senanayake, C. H.
Angewandte Chemie International Edition, 2015, 54, 5474.
3. Asymmetric Synthesis of All-Carbon Benzylic Quaternary Stereocenters via Conjugate Addition
to Alkylidene Meldrum’s Acids, Beaton, E.; Fillion, E.; Zhang, L.; Senanayake, C. H. Organic
Syntheses, 2015, 92, 182.
4. Efficient Synthesis of Empagliflozin, an Inhibitor of SGLT-2, Utilizing an AlCl3-Promoted Silane
Reduction of a β-Glycopyranoside, Wang, X-j; Zhang, L.; Byrne, D.; Nummy L.; Weber, D.;
Krishnamurthy, D.; Yee, N.; Senanayake, C. H. Organic Letters, 2014, 16, 4090.
5. Design and Synthesis of Chiral Oxathiozinone Scaffolds: Efficient Synthesis of Hindered
Enantiopure Sulfinamides and Sulfinyl Ketimines, Han, Z. S.; Herbage, M. A.; Mangunuru, H. P.
R.; Xu, Y.; Zhang, L.; Reeves, J. T.; Sieber, J. D.; Li, Z.; DeCroos, P.; Zhang, Y.; Li, G.; Li, N.;
Ma, S.; Grinberg, N.; Wang, X.; Goyal, N.; Krishnamurthy, D.; Lu, B.; Song, J. J.; Wang, G.;
Senanayake, C. H. Angew Chem Int 2013, 52, 6713.
6. Regioselective synthesis of polysubstituted N2-alkyl/aryl-1,2,3-triazoles via 4-bromo-5-iodo-
1,2,3-triazole, Zhang, L.; Li, Z.; Wang, X-j; Yee, N.; Senanayake, C. H. Synlett 2012, 23, 1052.
7. Practical synthesis of benzophenone-based NNRT inhibitor of HIV-1, Wang, X-j; Zhang, L.; Sun,
X.; Lee, H.; Krishnamurthy, D.; O'Meara, J. A.; Landry, S.; Yoakim, C.; Simoneau, B.; Yee, N.
K.; Senanayake, C. H. Organic Process Research & Development 2012, 16, 561.
8. Asymmetric Synthesis of LFA-1 Inhibitor BIRT2584 on Metric Ton Scale, Wang, X-j; Frutos, R.
P.; Zhang, L.; Sun, X.; Xu, Y.; Wirth, T.; Nicola, T.; Nummy, L. J.; Krishnamurthy, D.; Busacca,
C. A.; Yee, N.; Senanayake, C. H. Organic Process Research & Development 2011, 15, 1185.
9. A new and practical boronic acid catalyzed intramolecular cyclodehydration of ureas for the
synthesis of LFA-1 antagonists, Frutos, R. P.; Tampone, T.; Mulder, J. A.; Xu, Y.; Reeves, D.;
3. Wang, X-j; Zhang, L.; Krishnamurthy, D.; Senanayake, C. H. Tetrahedron Letters, 2011, 52,
2465.
10. Bis[2-(N,N-dimethylamino)ethyl] ether, Zhang, L.; Wang, X-j.; Krishnamurthy, D. K.;
Senanayake, C. H. Encyclopedia of Reagents for Organic Synthesis, 2011, 1.
11. General Solution to the Synthesis of N-2-Substituted 1,2,3-Triazoles, Wang, X.-j.; Zhang, L.;
Krishnamurthy, D.; Senanayake, C. H.; Wipf, P. Organic Letters, 2010, 12, 4632.
12. Efficient Synthesis of a Small Molecule, Nonpeptide Inhibitor of LFA-1, Wang, X.-j.; Xu, Y.;
Zhang, L.; Krishnamurthy, D.; Wirth, T.; Senanayake, C. Organic Letters, 2010, 12, 4412.
13. Palladium-Catalyzed Cross-Coupling of Cyclopropylmagnesium Bromide with Aryl Bromides
Mediated by Zinc Halide Additives, Shu, C.; Sidhu, K.; Zhang, L.; Wang, X-j; Krishnamurthy, D;
Senanayake, C. H. Journal of Organic Chemistry, 2010, 75, 6677.
14. Bromo-Directed N-2 Alkylation of NH-1,2,3-Triazoles: Efficient Synthesis of Poly-Substituted
1,2,3-Triazoles, Wang, X-j; Sidhu, K.; Zhang, L.; Campbell, S.; Haddad, N.; Reeves, D. C.;
Krishnamurthy, D; Senanayake, C. H. Organic Letters, 2009, 11, 5490.
15. Highly Regioselective N-2 Arylation of 4,5-Dibromo-1,2,3-triazole: Efficient Synthesis of 2-
Aryltriazoles, Wang, X.-j.; Zhang, L.; Lee, H.; Haddad, N.; Krishnamurthy, D.; Senanayake, C. Organic
Letters, 2009, 11, 5026.
16. An Improved Method of Amide Synthesis using Acyl Chlorides, Zhang, L.; Wang, X-j; Wang, J.;
Grinberg, N.; Krishnamurthy, D.; Senanayake, C. Tetrahedron Lett. 2009, 50, 2964.
17. The Chemistry of Ru cyclopropylmethylidene complexes: mechanistic studies and synthetic
implications for the ring-closing metathesis reaction, Farina, V.; Zeng, X.; Wei, X.; Xu, Y.;
Zhang, L.; Haddad, N.; Yee, N. K.; Senanayake, C. H. Catalysis Today, 2009, 140, 74.
18. Efficient synthesis of (S)-2-(cyclopentyloxycarbonyl)-amino-8-nonenoic acid: key building block
for BILN 2061, an HCV NS3 protease inhibitor, Wang, X-j; Zhang, L.; Smith-Keenan, L. L.;
Houpis, I. N.; Farina, V. Organic Process Research & Development, 2007, 11, 60.
19. Olefin ring-closing metathesis as a powerful tool in drug discovery and development - potent
macrocyclic inhibitors of the hepatitis C virus NS3 protease, Tsantrizos, Y. S.; Ferland, J-M;
McClory, A.; Poirier, M.; Farina, V.; Yee, N. K.; Wang, X-j; Haddad, N.; Wei, X.; Xu, J.; Zhang,
L. Journal of Organometallic Chemistry, 2006, 691, 5163.
20. Epimerization reaction of a substituted vinylcyclopropane catalyzed by ruthenium carbenes:
mechanistic analysis, Zeng, X.; Wei, X.; Farina, V.; Napolitano, E.; Xu, Y.; Zhang, L.; Haddad,
N.; Yee, N.; Grinberg, N.; Shen, S.; Senanayake, C. Journal of Organic Chemistry, 2006, 71,
8864.
21. Efficient large-scale synthesis of BILN 2061, a potent HCV protease inhibitor, by a convergent
approach based on ring-closing metathesis, Yee, N.; Farina, V.; Houpis, I.; Haddad, N.; Frutos, R.;
Gallou, F.; Wang, X.-j.; Wei, X.; Simpson, R.; Feng, X.; Fuchs, V.; Xu, Y.; Tan, J.; Zhang, L.;
Xu, J.; Smith-Keenan, L.; Vitous, J.; Ridges, M.; Spinelli, E.; Johnson, M.; Donsbach, K.; Nicola,
T.; Brenner, M.; Winter, E.; Kreye, P.; Samstag, W. Journal of Organic Chemistry, 2006, 71,
7133.
22. Mild iodine-Magnesium exchange of iodoaromatics bearing a pyrimidine ring with
isopropylmagnesium chloride, Wang, X.-j.; Xu, Y.; Zhang, L.; Krishnamurthy, D.; Senanayake,
C. Organic Letters, 2006, 8, 3141.
23. Noncryogenic I/Br-Mg exchange of aromatic halides bearing sensitive functional groups using i-
PrMgCl-bis[2-(N,N-dimethylamino)ethyl] ether complexes, Wang, X.-j.; Sun, X.;
Zhang, L.; Xu, Y.; Krishnamurthy, D.; Senanayake, C. Organic Letters, 2006, 8, 305.
24. Addition of Grignard reagents to aryl acid chlorides: an efficient synthesis of aryl
ketones, Wang, X.-j.; Zhang, L.; Sun, X.; Xu, Y.; Krishnamurthy, D.; Senanayake, C. Organic
Letters, 2005, 7, 5593.
25. Synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid vinyl-ACCA) derivatives: key
intermediates for the preparation of inhibitors of the hepatitis C virus NS3 protease, Beaulieu, P.
L.; Gillard, J.; Bailey, M. D.; Boucher, C.; Duceppe, J-S; Simoneau, B.; Wang, X.-j.; Zhang, L.;
Grozinger, K.; Houpis, I.; Farina, V.; Heimroth, H.; Krueger, T.; Schnaubelt, J. J. Org. Chem.,
2005, 70, 5869.
26. A practical synthesis of LFA-1 inhibitors utilizing CuCl-promoted intramolecular cyclization of
thiohydantoins, Wang, X.-j.; Zhang, L.; Xu, Y.; Krishnamurthy, D.; Varsolona, R.; Nummy, L.;
4. Shen, S.; Frutos, R.; Byrne, D.; Chung, J. C.; Farina V.; Senanayake C. Tetrahedron Lett. 2005,
46, 273.
27. A practical synthesis of highly functionalized fused 1,6-dihydroimidazo-[1,2-
a]imidazole-2,5-diones, key intermediates for LFA-1 inhibitors, Wang, X.-J.; Xu, Y.; Zhang,
L.; Krishnamurthy, D.; Nummy, L.; Farina, V.; Senanayake, C. SynLett, 2004, 15, 2800.
28. A practical synthesis of 2-(N-substituted)-aminobenzimidazoles utilizing CuCl-promoted
intramolecular cyclization of N-(2-aminoaryl)thioureas, Wang, X.-j.; Zhang, L.; Xu, Y.;
Krishnamurthy, D.; Senanayake C. Tetrahedron Lett. 2004, 45, 7167.
29. Regioselective synthesis of unsymmetrical 3,5-dialkyl-1-arylpyrazoles, Wang, X.-j.; Tan, J.;
Zhang, L. Organic Letters, 2000, 2, 3107.
PATENTS
1. Process for preparing [4,6-bis-dimethylamino-2-[4-(4-trifluoromethylbenzoylamino)benzyl]
pyrimidin-5-yl]acetic acid, Rodriguez Dehli, J. M.; Schul, M.; Stange, C.; Hagenkoetter, R.;
Wang, X-j.; Zhang, L.; Massot, O., U.S. (2014), US 8859770 B2 20141014.
2. Process for preparation of substituted 2-amino-5-[5-(heterocyclomethyl)pyridin-2-yloxy]benzoic
acid, Eriksson, M.; Krishnamurthy, D.; Wang, X-j.; Zhang, L.,
U.S. (2013), US 8410091 B1 20130402.
3. Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and
intermediates therein, Eckhardt, M.; Himmelsbach, F.; Wang, X.-j.; Sun, X.; Zhang, L.; Tang,
W.; Krishnamurthy, D.; Senanayake, C.; Han, Z., WO 2006120208 A1 20061116 AN
2006:1206861.
4. Process for preparation of oxoimidazoimidazolesulfonamides, Wang, X.-j.; Wirth, T.; Nicola, T.;
Zhang, L.; Frutos, R.; Xu, Y.; Krishnamurihy, D.; Nummy, L.; Varsolona, R..; Senanayake, C.;
Kroeber, J., US 2006025447 A1 20060202 CAN 144:192252 AN 2006:10468.
5. Process for preparing nitrogen-containing macrocyclic compounds, Busacca, C.; Farina, V.;
Gallou, F.; Haddad, N.; Wang, X-J; Wei, X.; Xu, J.; Xu, Y.; Yee, N. K.; Zhang, L. US
2005209135 A1 20050922 CAN 143:306296 AN 2005:1026593.
6. Synthesis of 6,7-dihydro-5H-imidazo[1,2a]imidazole-3-sulfonic acid amides, Frutos, R.;
Krishnamurthy D.; Nummy, L.; Nicola, T.; Varsolona, R.; Wirth, T.; Xu Y.; Zhang L.,
Provisional U.S. patent application (60/591,398) filled in July 27, 2004.
PRESENTATIONS
1. Process Driven Research: A Mild Version of Grignard Reagents and Its Applications, Zhang, L.
Professor Richard C. Larock Retirement Symposium, Ames, IA, United States, 2011.
2. Overcome the Limitation of Acyl Chloride in Amide Bond Formation and Peptide Coupling,
Zhang, L.; Wang, X-j; Krishnamurthy, D.; Senanayake, C. Poster Presentation, 234th ACS
National Meeting, Boston, MA, United States, 2007, ORGN-825.
3. Practical Synthesis of 2-(N-substituted)-aminobenzimidazoles and Highly Functionalized Bicyclic
Quanidines via CuCl-promoted Intramolecular Cyclization, Zhang, L.; Wang, X.-j.; Xu, Y.;
Krishnamurthy, D.; Senanayake C. Poster Presentation, 230th ACS National Meeting,
Washington, DC, United States, 2005, ORGN-392.
REFERENCES
Xiao-jun Wang, Senior Research Fellow, Boehringer-Ingelheim Pharmaceuticals, Inc. , 203-791-6199