Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Lithium Bromide | HCID 82050 | — |
| Reactant | HCID 131734112 | HCID 131734112 | — |
| Solvent | 1,3-Dimethyl-2-imidazolidinone | HCID 6661 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 131734114 | HCID 131734114 | 92.5% |
Reaction Steps
451 mg of lithium bromide was added to a solution of 1.15 g of (2R,3R,4R)-2-fluoro-3,5-bis((4-methoxybenzyl)oxy)-4-(2,4,5-trichlorophenoxy)pentan al O-methyloxime in 6 mL of tetrahydrofuran and 6 mL of 1,3-dimethyl-2-imidazolidinone, and the obtained mixture was then stirred at 65° C. for 7 hours. Thereafter, ethyl acetate and a 25% lithium bromide aqueous solution were added to the reaction mixture. The organic layer was fractionated, and it was washed with a 12% lithium bromide aqueous solution and was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 60/40), so as to obtain 857 mg of (2S,3S,4S)-4-bromo-2-fluoro-3,5-bis((4-methoxybenzyl)oxy)pentanal O-methyloxime in the form of a colorless oily product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09187514B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-253f27ee34224a0ba758c6b3cc5b4a30 |
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| Source note | uspto-grants-2015_11 |
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