- Chromatograms of the chlorohydrin ( 2) and the epoxide ( 3), tables of rate data for the initial kinetic studies, serial chromatograms showing (a) the reaction of the chlorohydrin ( 2) to the epoxide and the diol ( 7) at pH 11 (b) the reaction of the epoxide ( 3) with both sulfur nucleophiles separately and in a “one-pot” experiment, the concentration–time profile for the “one-pot” experiment, concentration–time profiles showing improved fitting of the sequential kinetics when dimerisation of the thiolate ( 4) is taken into account, concentrations of the reactants and products in the sequential experiment derived from the determination of the relative extinction coefficient of the thioether ( 6), HPLC peak area integral-time profile showing dimerisation of the thiolate ( 4) occurring in parallel to the desired reactions, HPLC peak area integral-time profile for the formation of bicalutamide ( 1) from the chlorohydrin ( 2) reacting via the epoxide ( 3) with 4-fluorobenzenesulfinate ( 5), reaction scheme for synthesis of the O-methyl analogue ( 8) and β-lactam ( 9), LCMS trace and high resolution MS for O-methyl analogue ( 8), MS fragmentation pattern and high resolution MS for β-lactam ( 9) PDF (339K)
- Article type
- 11 Sep 2008
- 10 Nov 2008
- First published
- 24 Dec 2008
Mechanistic studies on the synthesis of
N. Asaad and S. Fillery, Org. Biomol. Chem., 2009, 7, 678 DOI: 10.1039/B815894K
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