Hydrochloric Acid → HCID 25254148, compound

HRID 1097921Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

{4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-pyridin-2-yloxy}-acetic acid methyl ester (Example 120, 190 mg) was dissolved in MeOH (3 mL), and treated with 1N NaOH (0.87 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 light yellow amorphous solid (180 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-d8e882f2334b40dfa7d62d52fcfe6b04
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143280B2

Reaction notes

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