4-Chlorobenzoic Acid → HCID 24954600, compound

HRID 1967585Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:29])[CH2:5][N:6]([C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:14]([Cl:28])[CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[Cl:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=1>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][N:6]([C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[C:24]([C:35](=[O:36])[C:34]3[CH:38]=[CH:39][C:31]([Cl:30])=[CH:32][CH:33]=3)[CH:25]=2)=[C:14]([Cl:28])[CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of {[3,5-Dichloro-4-(4-methoxy-phenoxy)-phenyl]-ethoxycarbonyl-amino}-acetic acid ethyl ester (7.25 g, 0.016 mol) and 4-chlorobenzoic acid (5.13 g, 0.03 mol) in Eaton's reagent (25 mL) was heated at 60° C. for 16 h. The reaction mixture was poured over ice. The product was taken up in ethyl acetate, washed with water, brine, dried over sodium sulphate, filtered and concentrated to give the crude product, which was purified by column chromatography over flash silica gel (hexane:ethylacetate 90:10) to afford pure ({3,5-Dichloro-4-[3-(4-chloro-benzoyl)-4-methoxy-phenoxy]-phenyl}-ethoxycarbonyl-amino)-acetic acid ethyl ester. (3.36 g, 36% yield)

Workup

additionThe reaction mixture was poured over ice
washwashed with water, brine
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated
customto give the crude product, which
customwas purified by column chromatography over flash silica gel (hexane:ethylacetate 90:10)

Sources & evidence

ORD record: ord-6c94988941de457cb624290e0cd7cf44
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420851B2

Reaction notes

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