Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Lithium Bromide | HCID 82050 | — |
| Reactant | HCID 131734116 | HCID 131734116 | — |
| Solvent | 1,3-Dimethyl-2-imidazolidinone | HCID 6661 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 131734118 | HCID 131734118 | 76.4% |
Reaction Steps
1.52 g of lithium bromide was added to a solution of 8.97 g of (2R,3S)-5-(methoxyimino)-2-(((2,4,5-trichlorophenyl)sulfonyl)oxy)pentane-1,3-diyl dibenzoate in 17.9 mL of tetrahydrofuran and 16.1 mL of 1,3-dimethyl-2-imidazolidinone, and the obtained mixture was then stirred at 50° C. for 3 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 13% 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 75/25), so as to obtain 4.84 g of (2R,3S)-2-bromo-5-(methoxyimino)pentane-1,3-diyl dibenzoate 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-29f905b2114e427f9c6785fd55df745a |
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| Source note | uspto-grants-2015_11 |
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