1,4-Dioxane → HCID 68782457, compound

HRID 2266541Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([NH2:13])[CH:7]=1.C[O:16][C:17](=O)[CH:18]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][C:25]=1[Cl:34])[C:19](=O)[CH2:20][CH3:21].O1CCOCC1>O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:7]=1[C:17](=[O:16])[C:18]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:26][C:25]=1[Cl:34])=[C:19]([CH2:20][CH3:21])[NH:13]2

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of (3-amino-4-fluorophenoxy)acetic acid methyl ester (1.0 g), 2-(2-chloro-4-methanesulfonylbenzyl)-3-oxopentanoic acid methyl ester (2.1 g), polyphosphoric acid (10 g) and dioxane (10 mL) was heated at 130° C. for 18 hours. The mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (19:1 by volume) to afford title compound, 1.6 g.

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with ethyl acetate
washThe combined extracts were washed with saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure
customthe residue purified by column chromatography on silica gel
washeluting with a mixture of dichloromethane and methanol (19:1 by volume)

Sources & evidence

ORD record: ord-6478b0b5c4984128875c834b39c0aa65
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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