Ethyl Acetate → HCID 131734114, compound

HRID 1508615Notes

Reaction equation

[Br-:1].[Li+].[CH3:3][O:4][N:5]=[CH:6][C@@H:7]([F:41])[C@H:8]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)[C@H:9](OC1C=C(Cl)C(Cl)=CC=1Cl)[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.C(OCC)(=O)C>O1CCCC1.CN1CCN(C)C1=O>[CH3:3][O:4][N:5]=[CH:6][C@H:7]([F:41])[C@H:8]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)[C@@H:9]([Br:1])[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 65 °C

Procedure

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.

Workup

washit was washed with a 12% 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 60/40)

Sources & evidence

ORD record: ord-f956ce63628842ab9b970efdbccbdbb0
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221865B2

Reaction notes

Loading…