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1.
J Org Chem ; 84(8): 4735-4747, 2019 04 19.
Article in English | MEDLINE | ID: mdl-30352146

ABSTRACT

A multidisciplinary approach covering synthetic, physical, and analytical chemistry, high-throughput experimentation and experimental design, process engineering, and solid-state chemistry is used to develop a large-scale (kilomole) Suzuki-Miyaura process. Working against clear criteria and targets, a full process investigation and optimization package is described highlighting how and why key decisions are made in the development of large-scale pharmaceutical processes.


Subject(s)
Drug Design , Drug Industry , Pyrazines/chemical synthesis , Triazines/chemical synthesis , High-Throughput Screening Assays , Molecular Structure , Pyrazines/chemistry , Triazines/chemistry
2.
Chemistry ; 18(22): 6873-84, 2012 May 29.
Article in English | MEDLINE | ID: mdl-22529052

ABSTRACT

Enantiopure, Boc-protected alkoxyamines 12 and 13, derived from the readily available homoallylic alcohols 4 via a reaction that involves either inversion or retention of configuration, undergo a diastereoselective Pd-catalyzed ring-closing carbonylative amidation to produce isoxazolidines 16/17 (≤50:1 diastereoisomer ratio (d.r.)) that can be readily converted into the N-Boc-protected esters of ß-amino-δ-hydroxy acids and their γ-substituted homologues 37. The key carbonylative cyclization proceeds through an unusual syn addition of the palladium and the nitrogen nucleophile across the C=C bond (19→21), as revealed by the reaction of 15, which afforded isoxazolidine 18 with high diastereoselectivity.

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