Isopropyl Methanesulfonate Synthesis Essay

Ligands of intermediate steric bulk were designed to mimic metalloenzymes with histidine and carboxlyate binding sites. The reaction between tris(3-isopropylpyrazolyl)methane and butyllithium followed by SO3NMe3 in THF yielded the new ligand lithium tris(3-isopropylpyrazolyl)methane sulfonate (LiTpmsiPr). Various metal salts reacted with LiTpmsiPr to give the octahedral complexes M(TpmsiPr)2 (M = Zn, Cu, Ni, Co, Fe) in which each ligand has N,N,O binding to the metal. In the reaction between LiTpmsiPr and ZnCl2, in addition to the major product Zn(TpmsiPr)2, [LiTpmsiPrZnCl2]·2THF was also formed as a minor product with a tetrahedral zinc atom coordinated to either N,N,Cl,Cl in the solid phase or N,N,N,Cl in acetonitrile solution. Although TpmsiPr is coordinatively flexible and can act as a bipodal or tripodal ligand, it appears to favor the formation of octahedral L2M complexes.

AstraZeneca, R&D Charnwood, Bakewell Road, Loughborough, Leicestershire LE11 5RH, United Kingdom, Reaction Science Consulting, LLC, Suite 202/11 Deer Park Drive, Monmouth Junction, New Jersey 08852, U.S.A., Research Institute for Chromatography, Pres. Kennedypark 26, B-8500, Kortrijk, Belgium, Pfizer Global Research and Development, Analytical R&D, Ramsgate Road, Sandwich, Kent CT13 9NJ, United Kingdom, Schering-Plough, 556 Morris Avenue, Summit, New Jersey 07901-1330, U.S.A.,GlaxoSmithKline, Park Road, Ware, Hertfordshire SG12 0DP, United Kingdom, GlaxoSmithKline, Five Moore Drive, Research Triangle Park, North Carolina 27709-3398, U.S.A., Wyeth Research, 500 Arcola Road, Collegeville, Pennsylvania 19426, U.S.A., and F. Hoffmann-La Roche Ltd., Grenzacher Strasse, 4070 Basel, Switzerland

Org. Process Res. Dev., 2009, 13 (3), pp 429–433

DOI: 10.1021/op800192a

Publication Date (Web): January 14, 2009

Copyright © 2009 American Chemical Society

* Authors for corresondence. E-mail: andrew.teasdale@astrazeneca.com;steve.eyley@astrazeneca.com., †

AstraZeneca, R&D.

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Reaction Science Consulting, LLC.

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Research Institute for Chromatography.

, ⊥

Pfizer Global Research and Development, Analytical R&D.

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Schering-Plough.

, ◻

GlaxoSmithKline, U.K.

, ●

GlaxoSmithKline, U.S.A.

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Wyeth Research.

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F. Hoffmann-La Roche Ltd.

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