APURBA BHATTACHARYA

 

LABORATORY

Department of Chemistry

Texas A&M University

MSC 161, Kingsville, Texas 78363

(361) 593-2664 [kfab002@tamuk.edu]

                       

EDUCATION

 

Ph.D. Organic Chemistry, University of Texas at Austin: 1982

M.S. Chemistry, Indian Institute of Technology. Kanpur, India: 1976

B.S. Chemistry, Calcutta University, India: 1974

 

EMPLOYMENT

1999- present     Assistant Professor, Tx A&M University, Kingsville.

1997-1999         Group Leader, Bristol Myers Squibb, Central Process Research

1995-1997         Lead Chemist; Innovator Group, Hoechst.

1994-1995:        Staff Chemist, Hoechst-Celanese.

1990-1994:        Senior Research Chemist, Hoechst-Celanese.

1988-1990:        Research Fellow, Process Research and Development, Merck & Co., Inc.

1983-1988         Senior Research Chemist, Process Research and Development, Merck & Co., Inc.

 

ACADEMIC EXPERIENCE

 

Graduate Research Assistant, (1977-1982), Professor James K. Whitesell. Department of Chemistry, University of Texas at Austin. Asymmetric induction in carbon-carbon bond forming reaction was studied.

Very high asymmetric induction (92-99%) were achieved in the nucleophilic addition of chiral glyoxylate and pyruvate esters as well as concerted "-ene" and cycloaddition reactions.

Kinetic resolutions of simple olefins were accomplished via asymmetric "-ene" reactions.

Intramolecular Diels-Alder reactions were exploited for asymmetric synthesis

of a natural product , antibiotic "X-14547A"

 

Teaching Assistant     Undergraduate organic chemistry laboratory.

 

INDUSTRIAL EXPERIENCE

Discovered and developed novel silicon mediated quinone oxidation of aza-steroids successfully implemented for the production of PROSCARTM / PROPECIATM and other benign prostatic hypertrophy (BPH)-candidates.

Process Research and Development designing novel, practical and cost-effective synthesis of drug candidates from bench scale to commercialization.

Introduced efficient chiral phase-transfer technology to prepare either enantiomer of the drug candidate L-644, 711.

Devised and devoloped a unique amphoteric copolymer derived from vinylpyridine and acetoxystyrene.

Discovered and developed a waste-free synthesis of chiral ibuprofen via unprecedented diastereoreversal.

Discovered and developed a synthesis of D-p-hydroxyphenylglycine via a novel crystallization induced asymmetric transformation.

Identified and developed a new synthesis of 2-alkyl indanones.

Devised and developed a synthesis of cromolyn sodiumTM

Identified and developed a novel synthesis of 4-quinazolinones as pharmaceutical intermediates.

Involved in the development from bench scale to commercialization of a 20-step synthesis of Gd/Lu Texaphyrin, agent for MRI imaging, photosensitizer and photodynamic therapy of cancer.

 

AWARDS

 

Robert A.Welch Fellowship

Phi Kappa Phi Fellowship for academic excellence.

Outstanding teaching assistant award (1980)

National Scholarship (India)

 

PROFESSIONAL ACTIVITIES

 

American Chemical Society

Merck and Hoechst ambassador in University of Texas at Austin , Houston and

Texas A & M University.

 

PUBLICATIONS

 

1.      "Asymmetric Induction, Nucleophilic Addition to a Chiral Glyoxylate Ester", Whitesell, J. K.; Bhattacharya, A. ; and Henke, K., J. Chem. Soc. Chem. Commun., 988-89 (1982).

2.      "Asymmetric Induction. Ene Reactions of a Chiral Glyoxylate Ester", Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; and Henke, K., J. Chem. Soc. Chem. Commun., 17, 989-90 (1982)

3.   "A Glimpse Towards Asymmetric Induction", Bhattacharya, A., Diss. Abstr. Int. B, 43 (12, pt. 1), 3980 (1983)

4.      "Asymmetric Induction. Reduction, Nucleophilic Addition to and Ene Reaction of Chiral Alpha-Keto Esters", Whitesell, J. K.; Bhattacharya, A.; and Deyo, D., J  Chem. Soc. Chem. Commun., 15, 802 (1983)

5.      "Efficient Catalytic Asymmetric Alkylations. 2. Chiral Robinson Annulations via Phase-Transfer Catalysis", Bhattacharya, A.; Dolling, U.-H.; Grabowski, E. J. J.; Karady.; Ryan, K. M.; Weinstock, L. M., Angew. Chem., 98, 442-443 (1986)

6.      "Asymmetric Induction in the Ene Reaction of a Glyoxylate Ester of S-Phenyl Menthol", Whitesell, J. K.; Bhattacharya, A.; Chen, H. H.; Deyo, D.; James, D.; and Liu, C. L., Tetrahedron, 42 (11), 2993-3001 (1986).

7.      "Efficient Asymmetric Alkylations via Chiral Phase-Transfer Catalysis: Applications and Mechanism", Dolling, U.-H.; Hughes, D. L.; Bhattacharya, A.; Ryan, K. M.; Karady, S.; Weinstock, L. M.; and Grabowski, E. J. J., In: Starks, C. M., Editor, "Phase Transfer Catalysis; New Chemistry, Catalysts, and Applications, Chapter 7", ACS  Symp. Ser., 326, 67-81 (1987).

8.      "Efficient Asymmetric Alkylations via Chiral Phase-Transfer Catalysis. A Novel Dual Catalysis." Dolling, U.-H.; Hughes, D. L.; Bhattacharya, A.; Ryan, K. M.; Karady, S.; Weinstock. L. M.; Grenda, V. J.; and Grabowski, E. J. J., Catalysis of Organic Reactions, [edited by Paul N. Rylander, Hatedd Greenfield and Robert L. Augustine], 33, 65-86 (1988).

9.      "Silylation-Mediated Oxidation of 4-Aza-3-Ketosteroids with DDQ Proceeds via DDQ-Substrate Adducts", Bhattacharya, A.; DiMichele, L. M.; Dolling, U.-H.; Douglas, A. W.; and Grabowski, E. J. J.,  J. Am. Chem. Soc., 110, 3318-19 (1988).

10."DDQ Oxidation of Silyl Enol Ethers to Enones Proceeds via DDQ-Substrate Adducts", Bhattacharya, A.; DiMichele, L. M.; Dolling, U.-H.; Grabowski, E. J. J.; Grenda, V. J., J. Org. Chem., 54,6118-6120 (1989).

11."Silicon Assisted Quinone Oxidations Proceeds via Quinone-Substrate Adducts". Merck Speakers Program Brochure 1989-1990.

12. "Proscar ®" Merck Index, eleventh edition, 7888, 1989.

13. "Oxidation of 4-Aza-3-Ketosteroids". Bhattacharya, A., Centennial Year Edition, MSDRL Selected Publications.

14. "Acylimidazolides as Versatile Synthetic Intermediates for the Preparation of Sterically Congested Amides and Ketones: A Practical Synthesis of Proscar" Bhattacharya, A.; Williams, J. M.; Amato, J. S.; Dolling, U.-H.; and Grabowski, E. J. J., Synthetic Communications 30(17), 2683-2690, 1990.

15. "Crystallization Induced Asymmetric Transformation: Synthesis of D-p-Hydroxyphenylglycine" Bhattacharya, A.; Aruallo-Mcadams, C.; and Meier, M. B., Synthetic Communications, 24(17), 2449-2459, 1994.

16. "Methyl Glyoxylate" Encyclopedia of Reagents for Organic Synthesis (EROS), Bhattacharya, A.1994.

17. "Phenmenthyl Glyoxylate" Encyclopedia of Reagents for Organic Synthesis (EROS),  Bhattacharya, A. 1994.

 

PATENTS

 

1.   "An Enantiomer of a Substituted Fluorenyloxy Acetic Acid": U.S.4606760.

2.      "Enantiomers of a Substituted Fluorenyloxy Acetic Acid": EP-176947.

3.      "Preparation of Enantiomers of a Substituted Fluorenyloxy Acetic Acid": U.S. 45857357.

4.       "Steroid Dehydrogenation Process Intermediates" : U.S. 5116983.

5.      "Dehydrogenation of Azasteroids" : U.S. 5084574.

6.      "Preparation of 4-Azo-chol-1-ene-3, 20-dione derivatives as testosterone reductase inhibitors" EP-367502.

7.      "Process for the dehydrogenation of 3-oxo steroids (and especially 3-oxo-4aza steroids) in the 1,2-position using quinones and silylating agents, and quinone-steroid adduct intermediates" EP-298652.

8.      "Amphoteric Copolymer Derived from Vinylpyridine and Acetoxystyrene" U. S. 5210149.

9.      "Amphoteric Copolymer Derived from Vinylpyridine and Acetoxystyrene" U. S. 5304610.

10."Precipitation-Induced Asymmetric Transformation of Chiral Alpha-Amino Acids and salts thereof" EP-499376.

11."Racemization of an Enantiomerically Enriched a-Aryl Carboxylic Acid" U.S. 5332834.

12."Selective Precipitation of alpha arylcarboxylic acid salts" U.S. 5380867.

13."Process for the Productton of Calcium Salts of Hydantoic Acid. U.S.5338859.

14."Selective Precipitation of a arylcarboxylic acid salts" U.S. 5399707.

15."Process for preparing cyclic ketones" U.S. 5489712.

16. “Process for the preparation of dialkali metal cromoglycates” U.S. 5,508,451

17. “Preparation of 4-quinazolinones from N-acyl-b-aminoacids” U.S. 96-596794.

18. “Preparation of 5,6-dihydro-3H-pyrimidin-4-one derivatives” U.S. 96-595885.

19. “Three step process for preparing anthranilic acids from aniline” U.S. 96-593536.

20. “Improved process for azole antifungal intermediates” U.S. patent applied for; application no. GP 74.