Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrogen Peroxide | HCID 784 | — |
| Reactant | Di-tert-butyl N,N-Diisopropylphosphoramidite | HCID 853005 | — |
| Reactant | HCID 23618808 | HCID 23618808 | — |
| Reactant | HCID 66713252 | HCID 66713252 | — |
| Reactant | HCID 178418441 | HCID 178418441 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66713059 | HCID 66713059 | — |
Reaction Steps
To a solution of EXAMPLE 4A (540 mg) in tetrahydrofuran (5 ml) was added di-tert-butyl diisopropylphosphoramidite (0.84 ml) and 0.45 M 1H-tetrazole (7.91 ml) at 0° C. The mixture was stirred at room temperature for 1.5 hours and cooled to 0° C. 30% Hydrogen peroxide (0.82 ml) was added. The mixture was stirred at room temperature for 30 minutes. Ice water and sodium bissulfite (1.1 g) were added. The resulting mixture was diluted with dichloromethane and the organic layer was washed with water extensively until the water layer became pH neutral. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography, eluting with 0-66% ethyl acetate in dichloromethane to provide the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09006247B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-3620cc482de649f1a919141353c502a4 |
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| Source note | uspto-grants-2015_04 |
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