title: Chemical Synthesis of the ODM-201's Diastereomers through an Efficient Intramolecular 1,3-Dipolar Cycloaddition.
abstract: An efficient synthesis of ODM-201's diastereomers has been developed from (R)-methyl 3-hydroxybutanoate or (S)-methyl 3-hydroxybutanoate, respectively, with high overall yield and excellent diastereomeric purity. The key step in this synthesis is the preparation of the key intermediate (R)-5-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1H-pyrazole-3-carboxylic acid or (S)-5-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1H-pyrazole-3-carboxylic acid through intramolecular 1,3-dipolar cycloaddition of the vinyl diazo carbonyl compounds.
authors.affiliation: State Key Lab of New Drug & Pharmaceutical Process, State Institute of Pharmaceutical Industry.
authors.forename: Tingting
authors.initials: T
authors.lastname: Pan
authors.affiliation: Chia Tai Tianqing Pharmaceutical Group Co., Ltd.
authors.forename: Chunguang
authors.initials: C
authors.lastname: Xia
authors.affiliation: State Key Lab of New Drug & Pharmaceutical Process, State Institute of Pharmaceutical Industry.
authors.forename: Huijuan
authors.initials: H
authors.lastname: Jiang
authors.affiliation: State Key Lab of New Drug & Pharmaceutical Process, State Institute of Pharmaceutical Industry.
authors.forename: Zhongtang
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: State Key Lab of New Drug & Pharmaceutical Process, State Institute of Pharmaceutical Industry.
authors.forename: Xueyan
authors.initials: X
authors.lastname: Zhu
authors.affiliation: State Key Lab of New Drug & Pharmaceutical Process, State Institute of Pharmaceutical Industry.
authors.forename: Yulei
authors.initials: Y
authors.lastname: Yang
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D061565:Cycloaddition Reaction; D006801:Humans; D008297:Male; D066244:Proton Magnetic Resonance Spectroscopy; D011720:Pyrazoles / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D011720:Pyrazoles; C000607739:darolutamide
keywords: ODM-201; diastereomer; intramolecular 1,3-dipolar cycloaddition; synthesis