Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 18-Crown-6 | HCID 28557 | — |
| Reactant | Sodium Benzoate | HCID 517055 | — |
| Reactant | HCID 90248153 | HCID 90248153 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 131733327 | HCID 131733327 | 62.8% |
Reaction Steps
Chiral (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,4-difluor-O-2-(iodomethyl)-4-methyl-tetrahydrofuran-3-yl benzoate (0.56 g, 1.15 mmol), sodium benzoate (0.825 g, 5.73 mmol) and 18-crown-6 (0.03 g, 0.115 mmol) were suspended in DMSO (20 mL), the solution was heated to 100° C. and stirred under nitrogen atmosphere for 18 h, then cooled to r.t., water (30 mL) was added into it, the mixture was extracted by EA (30 mL×3), the organic layer was washed with H2O, brine and H2O, removed solvent by reduced pressure, the residue was purified by silica gel column chromatography (PE:EA=1:2) to afford the title compound as a colorless oil (0.34 g, 61%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09108999B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-666cef6f3e524d5caead6d5ab36b98c9 |
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| Source note | uspto-grants-2015_08 |
|---|