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Use of Lipase Catalytic Resolution in the Preparation of Ethyl (2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxylate, a Key Intermediate of the β-Lactamase Inhibitor Avibactam

PROCESS, SYNTHESIS Comments Off

Nov 242018

Here we describe an efficient and cost-effective chemoenzymatic synthesis of the β-lactamase inhibitor avibactam starting from commercially available ethyl 5-hydroxypicolinate hydrochloride. Avibactam was synthesized in 10 steps with an overall yield of 23.9%. The synthetic route features a novel lipase-catalyzed resolution step during the preparation of (2S,5S)-ethyl 5-hydroxypiperidine-2-carboxylate, a valuable precursor of the key intermediate ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. Our synthetic route was used to produce 400 g of avibactam sodium salt.

Use of Lipase Catalytic Resolution in the Preparation of Ethyl (2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxylate, a Key Intermediate of the β-Lactamase Inhibitor Avibactam

Tao Wang^†^§, Liang-Dong Du^‡, Ding-jian Wan^‡, Xiang Li^‡, Xin-Zhi Chen*^§

, and Guo-Feng Wu*^†

^† Research &Development Center, Zhejiang Medicine Co., Ltd, 59 East Huangcheng Road, Xinchang, Zhejiang 312500, P. R. China

^‡ Shanghai Laiyi Center for Biopharmaceuticals R&D, 5B, Building 8 200 Niudun Road Pudong District, Shanghai 201203, P. R. China

^§ Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Zhejiang University, 38 Zhejiang University Road, Xihu District, Hangzhou 310007, P. R. China

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.8b00173

Publication Date (Web): November 5, 2018

*E-mail: xcwuyuanzhang@163.com., *E-mail: xzchen@zju.edu.cn.

https://pubs.acs.org/doi/10.1021/acs.oprd.8b00173

///////////lipase, resolution, avibactam

Enzymatic resolution of antidepressant drug precursors in an undergraduate laboratory

drugs, spectroscopy, SYNTHESIS Comments Off

Apr 012015

Enzymatic resolution of antidepressant drug precursors in an undergraduate laboratory

EducaçãoQuim. Nova 2015, 38(2), 285-287

Enzymatic resolution of antidepressant drug precursors in an undergraduate laboratory

Luís M. R. SolanoI; Nuno M. T. LourençoII,*

This paper describes a multi-step chemo-enzymatic synthesis of antidepressant drug precursors.

http://dx.doi.org/10.5935/0100-4042.20140306

Publicado online: novembro 13, 2014

Quim. Nova, Vol. 38, No. 2, 285-287, 2015

Educação http://dx.doi.org/10.5935/0100-4042.20140306

*e-mail: nmtl@tecnico.ulisboa.pt

ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY

Luís M. R. Solanoa and Nuno M. T. Lourençob,* a Faculdade de Farmácia da Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal b Departamento de Bioengenharia, Instituto de Biotecnologia e Bioengenharia, Instituto Superior Técnico, Av. Rovisco Pais, 1, 1049-001 Lisboa, Portugal

Recebido em 07/07/2014; aceito em 17/09/2014; publicado na web em 13/11/2014

The use of biocatalysts in synthetic chemistry is a conventional methodology for preparing enantiomerically enriched compounds. Despite this fact, the number of experiments in chemical teaching laboratories that demonstrate the potential of enzymes in synthetic organic chemistry is limited. We describe a laboratory experiment in which students synthesized a chiral secondary alcohol that can be used in the preparation of antidepressant drugs. This experiment was conducted by individual students as part of a Drug Synthesis course held at the Pharmacy Faculty, Lisbon University. This laboratory experiment requires six laboratory periods, each lasting four hours. During the first four laboratory periods, students synthesized and characterized a racemic ester using nuclear magnetic resonance spectroscopy and gas chromatography. During the last two laboratory periods, they performed enzymatic hydrolysis resolution of the racemic ester using Candida antarctica lipase B to yield enantiomerically enriched secondary alcohol. Students successfully prepared the racemic ester with a 70%-81% overall yield in three steps. The enzymatic hydrolysis afforded (R)- secondary alcohol with good enantioselectivity (90%–95%) and reasonable yields (10%–19%). In these experiments, students were exposed to theoretical and practical concepts of aromatic acylation, ketone reduction, esterification, and enzymatic hydrolysis. Keywords: sec-alcohols; esters; lípase; enantiomers; resolution.

READ AT

http://quimicanova.sbq.org.br/imagebank/pdf/v38n2a20.pdf

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DR ANTHONY MELVIN CRASTO Ph.D amcrasto@gmail.com

MOBILE-+91 9323115463

GLENMARK SCIENTIST , NAVIMUMBAI, INDIA

……………………………………. DR ANTHONY MELVIN CRASTO Ph.D , Born in Mumbai in 1964 and graduated from Mumbai University, Completed his PhD from ICT ,1991, Mumbai, India in Organic chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARKPHARMA LTD, Research centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Prior to joining Glenmark, he worked with major multinationals like Hoechst Marion Roussel, now Sanofi Aventis, & Searle India ltd, now Rpg lifesciences, etc. He has worked in Basic research, Neutraceuticals, Natural products, Flavors, Fragrances, Pheromones, Vet Drugs, Drugs, formulation, GMP etc. He has total 25 yrs exp in this field, he is now helping millions, has 9 million hits on google on all organic chemistry websites. His New Drug Approvals , Green Chemistry International, Eurekamoments in Organic Chemistry , Organic Chemistry by Dr Anthony, WIX BLOG , are some most read chemistry blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 29 year tenure, good knowledge of IPM, GMP, Regulatory aspects, he has several international drug patents published worldwide . He has good proficiency in Technology Transfer, Spectroscopy , Stereochemistry , Synthesis, Reactions in Org Chem , Polymorphism, Pharmaceuticals , Medicinal chemistry , Organic chemistry literature , Patent related site , Green chemistry , Reagents , R & D , Molecules , Heterocyclic chem , Sourcing etc He suffered a paralytic stroke in dec 2007 and is bound to a wheelchair, this seems to have injected feul in him to help chemists around the world, he is more active than before and is pushing boundaries, he has 2.5 lakh connections on all networking sites, He makes himself available to all, contact him on +91 9323115463, amcrasto@gmail.com