1,4-Dioxane → HCID 68780024, compound

HRID 2266531Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([NH2:13])[CH:7]=1.C([O:17][C:18](=O)[CH:19]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1)[C:20](=O)[CH:21]([CH3:23])[CH3:22])C.O1CCOCC1>O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]2[C:7]=1[C:18](=[O:17])[C:19]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([S:32]([CH3:35])(=[O:33])=[O:34])=[CH:30][CH:31]=1)=[C:20]([CH:21]([CH3:22])[CH3:23])[NH:13]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (3-amino-4-chlorophenoxy)acetic acid methyl ester (0.70 g), 2-(4-methanesulfonylbenzyl)-4-methyl-3-oxopentanoic acid ethyl ester (1.4 g), polyphosphoric acid (3.5 g) and dioxane (50 mL) was heated at 120° C. for 2 days. The mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (1:1 by volume) to afford title compound. 0.79 g.

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with ethyl acetate
dry with materialThe combined extracts were dried over magnesium sulfate
customthe solvent removed under reduced pressure
customThe residue was purified by column chromatography on silica gel
washeluting with a mixture of ethyl acetate and cyclohexane (1:1 by volume)

Sources & evidence

ORD record: ord-ad0fb5b9f41246d3b59126c4bbff210f
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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