Methanesulfonic Acid → HCID 68783011, compound

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]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:20](=O)[CH2:21][CH3:22])C.CS(O)(=O)=O>C1(C)C=CC=CC=1>[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]([CH2:24][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

Procedure

A mixture of (3-amino-4-chlorophenoxy)acetic acid methyl ester (0.53 g), 2-(4-chlorobenzyl)-3-oxopentanoic acid ethyl ester (0.66 g), methanesulfonic acid (0.032 mL) and toluene (20 mL) was heated at reflux for 20 hours. The mixture was cooled to room temperature and the solvent removed under reduced pressure. The residue was diluted with water, extracted with ethyl acetate and the combined extracts 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 (9:1 by volume) to afford title compound, 0.034 g