HCID 66717606, compound → HCID 68783178, compound

HRID 2266546Notes

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:17][C:18](=O)[CH:19]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:20](=O)[CH2:21][CH3:22])C>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:18](=[O:17])[C:19]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=1)=[C:20]([CH2:21][CH3:22])[NH:13]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (3-amino-4-fluorophenoxy)acetic acid methyl ester (1.9 g), 2-(4-chlorobenzyl)-3-oxopentanoic acid ethyl ester (0.95 g) and polyphosphoric acid (10 mL) was heated at 120° C. for 5 hours. The mixture was diluted with water, extracted with ethyl acetate and the combined extracts washed with saturated aqueous sodium chloride solution and saturated aqueous sodium hydrogen carbonate solution and then 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 ethyl acetate (1:0 to 10:1 by volume) to afford title compound as a brown solid, 0.10 g.

Workup

extractionextracted with ethyl acetate
washthe combined extracts washed with saturated aqueous sodium chloride solution and saturated aqueous sodium hydrogen carbonate 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 ethyl acetate (1:0 to 10:1 by volume)

Sources & evidence

ORD record: ord-48d12264b4a242f19e9703a862b6cf82
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

Loading…