Acetone → Methyl 4-{1,2-dihydroxy-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}benzoate

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To a solution of the product from Step 1 (0.100 g, 0.201 mmol) and 4-methylmorpholine n-oxide (0.047 g, 0.403 mmol) in acetone (2.98 ml)/water (0.373 ml) was added osmium tetroxide (4% by weight in water, 0.158 ml, 0.020 mmol), and the mixture was stirred at room temperature. Upon completion by LCMS, the mixture was diluted with aqueous 10% Na2SO3 and EtOAc. The aqueous layer was acidified (pH 3-4) with 1 N HCl and extracted with 10% IPA/CHCl3. The combined organic layers were dried (Na2SO4), filtered and concentrated. A combination of chromatography on silica gel (Biotage 250 SNAP, 0-10% MeOH/DCM) and reverse phase HPLC (10-90% ACN/1-120) afforded methyl 4-{1,2-dihydroxy-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}benzoate (70 mg, 0.132 mmol, 65.5% yield). MS ESI: [M+H]+ m/z 531.1.

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