Hydrochloric Acid → HCID 46245545, compound

HRID 1673526Notes

Reaction equation

[OH-].[Na+].C(O)C.[CH3:6][O:7][C:8]1[CH:32]=[CH:31][C:11]([C:12]([NH:14][C:15]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:22]=[CH:21][C:16]=2[C:17]([O:19]C)=[O:18])=[O:13])=[CH:10][CH:9]=1.Cl>C(OCC)(=O)C>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:14][C:15]2[CH:24]=[C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:22]=[CH:21][C:16]=2[C:17]([OH:19])=[O:18])=[O:13])=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 40 °C

Procedure

1.0 mL of 2.0 mol/L aqueous sodium hydroxide and 3.0 mL of ethanol were added to the obtained methyl 2-(4-methoxybenzamido)-4-phenylbenzoate and stirred at 40° C. for 2 hours. After the reaction mixture was cooled to room temperature, 8.0 mL of 0.38 mol/L hydrochloric acid and 10 mL of ethyl acetate were added. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 55-100% acetonitrile /0.1% trifluoroacetic acid aqueous solution] to obtain 6.1 mg of 2-(4-methoxybenzamido)-4-phenylbenzoic acid as white solid.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customThe organic layer was separated
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 55-100% acetonitrile /0.1% trifluoroacetic acid aqueous solution]

Sources & evidence

ORD record: ord-ae25d9ef1bcc43a5b1e1fdb1dbfc526e
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999132B2

Reaction notes

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