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

HRID 2238327Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=NN=N1.C(N(CC)[P:24]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])C.ClC1C=CC=C(C(OO)=[O:45])C=1>ClCCl.C(Cl)(Cl)Cl>[P:24]([O:13][CH2:12][C:11]([CH3:15])([CH3:14])[CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:45]

Participants

Conditions

Temperature: -45 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-94ef3185c8b34e4fa6ebfd1514a91471
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718633B2

Reaction notes

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