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Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors

Santosh K. Singh, Narendra Manne and Manojit Pal

Beilstein J. Org. Chem. 2008, 4, No. 20. https://doi.org/10.3762/bjoc.4.20

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Supporting Information File 1: ¹H and ¹³C NMR spectra of compound 6 in CDCl₃.
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Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors

Santosh K. Singh, Narendra Manne and Manojit Pal

Beilstein J. Org. Chem. 2008, 4, No. 20. https://doi.org/10.3762/bjoc.4.20

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Singh, S. K.; Manne, N.; Pal, M. Beilstein J. Org. Chem. 2008, 4, No. 20. doi:10.3762/bjoc.4.20

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Reddy, B. K. K.; Sekhar, K. B. C.; Mohan, C. K. Bioanalytical Method Development and Validation for the Simultaneous Determination of Vildagliptin and Telmisartan in Rabbit Plasma Using RP-HPLC. Journal of Pharmaceutical Research International 2021, 76–86. doi:10.9734/jpri/2021/v33i131141
Pal, S.; Pal, M. Anti-diabetes Research in India: Contributions from Industrial Organizations. Drug Discovery and Drug Development; Springer Singapore, 2021; pp 179–212. doi:10.1007/978-981-15-8002-4_8
Arar, S.; Al-Qudah, E.; Al-Zweiri, M.; Sweidan, K. New forced degradation products of vildagliptin: Identification and structural elucidation using LC-MS, with proposed formation mechanisms. Journal of Liquid Chromatography & Related Technologies 2020, 1–12.
Arar, S.; Al-Qudah, E.; Alzweiri, M.; Sweidan, K. New forced degradation products of vildagliptin: Identification and structural elucidation using LC-MS, with proposed formation mechanisms. Journal of Liquid Chromatography & Related Technologies 2020, 43, 633–644. doi:10.1080/10826076.2020.1779084
Wakaki, T.; Sakai, K.; Enomoto, T.; Kondo, M.; Masaoka, S.; Oisaki, K.; Kanai, M. C(sp3 )-H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis. Chemistry (Weinheim an der Bergstrasse, Germany) 2018, 24, 8051–8055. doi:10.1002/chem.201801746
Biftu, T.; SinhaRoy, R. DPP-4 Inhibitors. Comprehensive Medicinal Chemistry III; Elsevier, 2017; Vol. 7, pp 512–555. doi:10.1016/b978-0-12-409547-2.12443-6
Stockdale, T. P.; Williams, C. M. Pharmaceuticals that contain polycyclic hydrocarbon scaffolds. Chemical Society reviews 2015, 44, 7737–7763. doi:10.1039/c4cs00477a
Jansen, K.; Heirbaut, L.; Verkerk, R.; Cheng, J. D.; Joossens, J.; Cos, P.; Maes, L.; Lambeir, A.-M.; De Meester, I.; Augustyns, K.; Van der Veken, P. Extended Structure–Activity Relationship and Pharmacokinetic Investigation of (4-Quinolinoyl)glycyl-2-cyanopyrrolidine Inhibitors of Fibroblast Activation Protein (FAP). Journal of medicinal chemistry 2014, 57, 3053–3074. doi:10.1021/jm500031w
Mohammad, M. A.-A.; Elkady, E. F.; Fouad, M. A. Development and validation of a reversed-phase column liquid chromatographic method for simultaneous determination of two novel gliptins in their binary mixtures with Metformin. European Journal of Chemistry 2012, 3, 152–155. doi:10.5155/eurjchem.3.2.152-155.570
El-Bagary, R. I.; Elkady, E. F.; Ayoub, B. M. Liquid Chromatographic Methods for the Determination of Vildagliptin in the Presence of its Synthetic Intermediate and the Simultaneous Determination of Pioglitazone Hydrochloride and Metformin Hydrochloride. International journal of biomedical science : IJBS 2011, 7, 201–208.
Jain, S. K.; Vishwakarma, S.; Nayak, P.
Tahrani, A. A.; Piya, M. K.; Barnett, A. H. Drug evaluation: vildagliptin-metformin single-tablet combination. Advances in therapy 2009, 26, 138–154. doi:10.1007/s12325-009-0010-0

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)