m-Chloroperbenzoic acid → Di-tert-butyl 4-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylbutyl phosphate

Temperature

-45 °C

To a solution of the product from Example 10A (0.630 g, 2.7 mmol) and 1H-tetrazole (0.568 g) in dichloromethane (11.0 mL) at room temperature was added di-t-butyl diethylphosphoramidite (1.02 g), and the solution was allowed to stir for 1 hour. The solution was cooled to −45° C., followed by addition of m-chloroperbenzoic acid (1.33 g). After 1 hour at −45° C., additional m-chloroperbenzoic acid (1.33 g) was added and the mixture was allowed to warm to room temperature and was stirred for 16 hours. The reaction mixture was diluted with chloroform and washed with 10% Na2CO3 and brine, and was dried over MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with 20% ethyl acetate in hexane, to give the title compound (0.441 g, 38%).

1. waitAfter 1 hour at −45° C.
2. temperatureto warm to room temperature
3. stirringwas stirred for 16 hours
4. washwashed with 10% Na2CO3 and brine
5. dry with materialwas dried over MgSO4
6. filtrationfiltered
7. customevaporated
8. customThe residue was purified by chromatography on silica gel
9. washeluting with 20% ethyl acetate in hexane

ORD record

ord-94ef3185c8b34e4fa6ebfd1514a91471

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07718633B2