Ethyl Acetate → HCID 131734118, compound

HRID 1508631Notes

Reaction equation

[Br-:1].[Li+].[C:3]([O:11][CH2:12][C@@H:13](OS(C1C=C(Cl)C(Cl)=CC=1Cl)(=O)=O)[C@@H:14]([O:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:15][CH:16]=[N:17][O:18][CH3:19])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OCC)(=O)C>O1CCCC1.CN1CCN(C)C1=O>[C:3]([O:11][CH2:12][C@@H:13]([Br:1])[C@@H:14]([O:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:15][CH:16]=[N:17][O:18][CH3:19])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

washit was washed with a 13% lithium bromide aqueous solution
dry with materialwas then dried over anhydrous sodium sulfate
distillationAfter that, the solvent was distilled away under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 75/25)

Sources & evidence

ORD record: ord-e81e6dcf37e14c0987010e8c1966e176
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221865B2

Reaction notes

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