Water → (2S,3S,4S)-4-bromo-2-fluoro-3,5-bis(benzyloxy)pentanal O-methyloxime

HRID 1508611Notes

Reaction equation

[Br-:1].[Li+].[CH3:3][O:4][N:5]=[CH:6][C@@H:7]([F:37])[C@H:8]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@H:9](OC1C=C(Cl)C(Cl)=CC=1Cl)[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCC)(=O)C.O>O1CCCC1.CN1CCN(C)C1=O>[CH3:3][O:4][N:5]=[CH:6][C@H:7]([F:37])[C@H:8]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@@H:9]([Br:1])[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

430 mg of lithium bromide was added to a solution of 1.50 g of (2R,3R,4R)-2-fluoro-3,5-bis(benzyloxy)-4-(2,4,5-trichlorophenoxy)pentanal O-methyloxime in 6 mL of tetrahydrofuran and 5.4 mL of 1,3-dimethyl-2-imidazolidinone, and the obtained mixture was then stirred at 60° C. for 6 hours. Thereafter, ethyl acetate and water were added to the reaction mixture. The organic layer was fractionated. The obtained organic layer was washed with a saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate. 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 662 mg of (2S,3S,4S)-4-bromo-2-fluoro-3,5-bis(benzyloxy)pentanal O-methyloxime in the form of a colorless oily product.

Workup

washThe obtained organic layer was washed with a saturated sodium chloride aqueous solution
dry with materialwas then dried over anhydrous magnesium sulfate
distillationThe 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-4ea288482b4649af9b1ce41344ed6e6e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221865B2

Reaction notes

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