Hydrochloric Acid → {4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-2-oxo-2H-pyridin-1-yl}-acetic acid

HRID 333815Notes

Reaction equation

C[O:2][C:3](=[O:28])[CH2:4][N:5]1[CH:10]=[CH:9][C:8]([C:11]([OH:26])([C:22]([F:25])([F:24])[F:23])[CH:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[CH3:13])=[CH:7][C:6]1=[O:27].[OH-].[Na+].Cl>CO>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[CH:12]([CH3:13])[C:11]([C:8]1[CH:9]=[CH:10][N:5]([CH2:4][C:3]([OH:28])=[O:2])[C:6](=[O:27])[CH:7]=1)([OH:26])[C:22]([F:23])([F:24])[F:25]

Participants

Conditions

Temperature: 55 °C

Procedure

{4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-2-oxo-2H-pyridin-1-yl}-acetic acid methyl ester (Example 121, 40 mg) was dissolved in MeOH (1 mL), and treated with 1N NaOH (0.183 mL). The reaction mixture was stirred at 55° C. (Bath temperature) for 2 h. The reaction mixture was then cooled down to r.t., pH adjusted to pH2 by addition of 1N aqueous HCl, and the MeOH evaporated in vacuo. The resulting suspension was then extracted twice with ethyl acetate, the combined organic phases washed with brine, dried over MgSO4 and concentrated in vacuo, leading to the title compound as off-white solid (33 mg). MS (m/e)=424.1 (MH+).

Workup

temperatureThe reaction mixture was then cooled down to r.t.
customthe MeOH evaporated in vacuo
extractionThe resulting suspension was then extracted twice with ethyl acetate
washthe combined organic phases washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-80b6d425ecf64b34adc173f1076050f8
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883786B2

Reaction notes

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