Hydrogen Peroxide → HCID 86707931, compound

Participants

Reaction Steps

To a solution of 2-(2-(1-(2,6-dichlorophenyl)-1-methylethyl)-1-(3,3′-difluoro-4′-(hydroxymethyl)-5′-(methylsulfonyl)-4-biphenylyl)-1H-imidazol-4-yl)-2-propanol (prepared in the manner described in PCT Publication No. WO 2010/138598, 1.98 g, 3.25 mmol) and di-tert-butyl diisopropylphosphoramidite (1.35 g, 4.87 mmol) in CH2CH2 (10 mL) was added tetrazole (0.569 g, 8.13 mmol). The resulting suspension was stirred at rt for about 16 hours. After this time, hydrogen peroxide (30%, 8.13 mmol) was added drop-wise and the resulting mixture was stirred for 2 hours. At the conclusion of this period, the reaction mixture was diluted with CH2CH2 (10 mL), washed with brine, dried and then concentrated to yield the crude product. The crude product was purified by column chromatography (hexane and acetone gradient; 9:1 to 1:1) to afford di-tert-butyl (4′-(2-(2-(2,6-dichlorophenyl)propan-2-yl)-4-(2-hydroxypropan-2-yl)-1H-imidazol-1-yl)-3,3′-difluoro-5-(methylsulfonyl)biphenyl-4-yl)methyl phosphate (0.960 g, 1.20 mmol, 37% yield) as a white solid.

Provenance & Evidence