Water → HCID 58452692, compound

HRID 70687Notes

Reaction equation

Cl[Si](C)(C)C.[I-].[K+].[Cl:8][C:9]1[CH:10]=[CH:11][C:12](/[C:17](/[C:25]2[CH:30]=[CH:29][C:28]([CH2:31][OH:32])=[CH:27][CH:26]=2)=[CH:18]/[C@@H:19]2[NH:23][C:22](=[O:24])[CH2:21][CH2:20]2)=[N:13][C:14]=1[O:15]C.O>C(#N)C>[Cl:8][C:9]1[C:14](=[O:15])[NH:13][C:12](/[C:17](/[C:25]2[CH:26]=[CH:27][C:28]([CH2:31][OH:32])=[CH:29][CH:30]=2)=[CH:18]/[C@H:19]2[CH2:20][CH2:21][C:22](=[O:24])[NH:23]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Chlorotrimethylsilane (0.123 mL) and potassium iodide (263 mg) were sequentially added to a solution of (5R)-5-{(E)-2-(5-chloro-6-methoxypyridin-2-yl)-2-[4-(hydroxymethyl)phenyl]ethenyl}pyrrolidin-2-one (142 mg) in acetonitrile (1.5 mL) at room temperature, after which the mixture was stirred at 60° C. for two hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (methanol:ethyl acetate=1:10) to give the title compound as a colorless solid (19 mg, 14%).

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customafter which the solvent was evaporated under reduced pressure
customThe residue was purified by silica gel chromatography (methanol:ethyl acetate=1:10)

Sources & evidence

ORD record: ord-2de7a1992787413c8f516be258f3f4d7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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