m-Chloroperbenzoic acid → Benzyl 1-(di-tert-butoxyphosphoryloxy)-2-phenylpropan-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

The product of Example 442A (2.7 mmol), di-tert-butyl diethylphosphoramidite (0.80 mL, 2.7 mmol), and 1-H-tetrazole (0.50 g, 6.8 mmol) in THF (25 mL) were reacted at room temperature for 12 hours. Subsequently the reaction was diluted with dichloromethane (25 mL) and cooled to −45° C. and followed by treatment with meta-chloroperoxybenzoic acid (0.66 g, 3.0 mmol) for 0.5 hours. The reaction was extracted with ethyl acetate (70 mL) and the organic extracts washed with 10% sodium carbonate (2×) and brine, dried over MgSO4, and concentrated. The residue was purified by chromatography on silica gel, eluting with a gradient of ethyl acetate in dichloromethane (0-25%) to give the title compound as a colorless oil (0.99 g, 78%).

Provenance & Evidence